• Chemical structure of (TBS)-Isopropylidene-D-ribonolactone, CAS 75467-36-6, ≥97% — chiral protected ribonolactone with TBS-ether and 2,3-O-isopropylidene protecting groups, used as a versatile building block in nucleoside synthesis, C-nucleoside chemistry, and stereoselective carbohydrate transformations. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.​​​​​​​​​​​​​​​​
  • ¹H NMR spectrum of (TBS)-Isopropylidene-D-ribonolactone (CAS 75467-36-6) in CDCl₃ at 298.1 K, Bruker Avance 400.15 MHz, 20 s relaxation delay, 8 scans. Ring C–H protons H2, H3 at ~4.7 ppm (2.00 + 1.00); H4 at ~4.6 ppm; H5 (CH₂–OTBS) at ~3.8–4.0 ppm (1.01 + 1.01); isopropylidene CH₃ groups at ~1.3 and ~1.4 ppm (3.01 + 3.00); Si–C(CH₃)₃ at ~0.9 ppm (9.11); Si(CH₃)₂ at ~0.1 ppm (6.18). Confirms structure and ≥97% purity. Batch NOR75467366-25-2, NorrChemica.
  • ¹³C NMR spectrum of (TBS)-Isopropylidene-D-ribonolactone (CAS 75467-36-6) in CDCl₃ at 298.1 K, Bruker Avance 100.63 MHz, 2 s relaxation delay, 2411 scans. Lactone C=O at 174.3 ppm; quaternary isopropylidene C(CH₃)₂ at 113.1 ppm; ring C–H carbons C2/C3/C4 at 82.4, 78.6 and 75.9 ppm; C5 (CH₂–OTBS) at 63.1 ppm; isopropylidene CH₃ at 26.9, 25.9 and 25.7 ppm; Si–C(CH₃)₃ at 18.3 ppm; Si(CH₃)₂ at –5.5 and –5.6 ppm. Confirms structure and ≥97% purity. Batch NOR75467366-25-2, NorrChemica.
  • gHMBC 2D NMR spectrum of (TBS)-Isopropylidene-D-ribonolactone (CAS 75467-36-6) in CDCl₃, Bruker Avance, correlating ¹H (F2, ~0–7.5 ppm) with ¹³C (F1, ~0–170 ppm) through long-range (²J, ³J) couplings. Cross-peaks from ring H2/H3/H4 (~4.5–4.7 ppm) and H5 (~3.8–4.0 ppm) to the lactone C=O (~174 ppm), the quaternary isopropylidene C (~113 ppm) and ring carbons (75–82 ppm) confirm the bicyclic framework; isopropylidene CH₃ and silyl groups correlate to expected aliphatic carbons. NorrChemica.
  • gHSQC 2D NMR spectrum of (TBS)-Isopropylidene-D-ribonolactone (CAS 75467-36-6) in CDCl₃, Bruker Avance, correlating ¹H (F2, ~0–8 ppm) with ¹³C (F1, ~20–170 ppm) one-bond couplings. Cross-peaks confirm ring C–H assignments H2/H3/H4 at ~4.5–4.7/75–82 ppm; H5 (CH₂–OTBS) at ~3.8–4.0/63 ppm; isopropylidene CH₃ at ~1.3–1.4/26 ppm; Si–C(CH₃)₃ at ~0.9/26 ppm; Si(CH₃)₂ at ~0.1/–6 ppm. Confirms structure of TBS- and isopropylidene-protected ribonolactone. NorrChemica.
1 5

NorrChemica™

TBS-Isopropylidene-D-ribonolactone

CAS 75467-36-6 ≥97%

TBS-Isopropylidene-D-ribonolactone | CAS 75467-36-6 | ≥97%

€23,75 EUR (incl. VAT)
€23,75 EUR
Sale Sold out
Taxes included. Shipping calculated at checkout.
Weight

Technical Specifications

CAS Number 75467-36-6
EC / EINECS Number 623-023-3
MDL Number MFCD00216623
SMILES CC1(O[C@@H]2[C@H](OC(=O)[C@@H]2O1)CO[Si](C)(C)C(C)(C)C)C
InChI InChI=1S/C14H26O5Si/c1-13(2,3)20(6,7)16-8-9-10-11(12(15)17-9)19-14(4,5)18-10/h9-11H,8H2,1-7H3/t9-,10-,11-/m1/s1
InChIKey VBPYRQYBEKHPKA-GMTAPVOTSA-N
PubChem CID 10913693
Molecular Formula C₁₄H₂₆O₅Si
Molecular Weight 302.44 g/mol
Melting Point 72-74 °C
Solubility Soluble in common organic solvents
Log Pow 2.45 (predicted, XLogP3)
Purity ≥97%
Physical Form White crystalline powder
HS Code 2932.20
Shelf Life Retest period: 24 months from date of manufacture
Storage Conditions Store at 2-8 °C in a tightly sealed container in a dry place

Product Description & Scientific Applications

TBS-Isopropylidene-D-ribonolactone (5-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone) is a dual-protected D-ribose-derived γ-lactone. The 5-hydroxyl is a fluoride-labile TBS ether, the 2,3-diol an acid-labile isopropylidene acetal, and the lactone carbonyl is free for C–C bond formation, reduction, and ring-opening. The bicyclic acetonide-fused ring holds the C2, C3, and C4 stereochemistry of D-ribose while C1 is elaborated — a rigid chiral-pool scaffold that biases facial selectivity at the carbonyl.

C-nucleoside synthesis. A carbon nucleophile — lithiated heteroarenes or Grignard reagents — adds to the lactone carbonyl to give a lactol, which is deoxygenated through a Lewis-acid oxocarbenium ion trapped by hydride or carbon to give the C-glycoside, replacing the natural C–N linkage with a C–C bond. Anomeric selectivity is set at the addition and at the oxocarbenium step, governed by the oxocarbenium conformation and the C2/C3 substituents; α:β is route-specific. The sequence builds uracil, maleimide, deazapurine, pyrazolopyrimidine, and pyrrolotriazine C-glycoside scaffolds.

Lactone elaboration. Low-temperature DIBAL-H reduction gives the lactol, a branch point for further C-nucleophile addition, reductive deoxygenation with triethylsilane and a Lewis acid, or O-acetylation or fluoride at the anomeric position. Stronger reduction opens the lactone to protected polyols, and olefination or homologation extends the ribose skeleton — routes to branched-chain sugars, deoxy-ribose variants, and protected polyhydroxylated targets.

Orthogonal deprotection. The TBS ether comes off with fluoride (TBAF, HF·pyridine, or triethylamine trihydrofluoride) to expose the primary 5-OH for oxidation, phosphorylation, or chain extension; the acetonide comes off under mild acid to reveal the 2,3-cis-diol. The two handles are staged independently, so the 5-OH, the diol, and the lactone each enter the sequence on demand.

Shipping Destinations

  • EU & UK: Priority delivery, 2–5 business days.
  • United States (DDP): 3–7 business days, duties and taxes prepaid.
  • EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
  • Worldwide: 7–14 business days, selected locations.

Safety Information

Hazard Class None — not subject to transport regulations
Transport Category Not classified as dangerous goods for transport (ADR/IATA/IMDG)

Documentation

Safety Data Sheet Download PDF
View full details