102339-30-0

Basic information

• Product Name: (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-ol
• Synonyms: (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-ol
• CAS NO: 102339-30-0
• Molecular Weight: 344.408
• Mol File: 102339-30-0.mol

Chemical Properties

• CAS DataBase Reference: (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-ol(102339-30-0)
• EPA Substance Registry System: (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-2-methoxytetrahydrofuran-3-ol(102339-30-0)

Safety Data

• Hazardous Substances Data: 102339-30-0(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 41341-99-5 3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 67-56-1 methanol 
• 16054-77-6 3,5-di-O-benzyl-D-xylofuranose 

Downstream Products

• 197716-38-4 2,3,5-tri-O-benzyl-1-O-methyl-D-xylofuranoside 
• 210548-16-6 methyl 2-benzoyl-3,5-dibenzyl-α,β-D-xylopyranoside 
• 211557-52-7 1-O-methyl 2-O-tosyl 3,5-di-O-benzyl α,β(D)xylo-pentoaldofuranose 
• 1061715-44-3 C₃₆H₄₂O₅Si 
• 259877-35-5 (2R,3R,5S)-5-allyl-3-(benzyloxy)-2-(benzyloxymethyl)tetrahydrofuran 
• 32469-86-6 Methyl-2-O-methyl-α-D-xylofuranosid 
• 95990-87-7 1-O-Methyl-3,5-di-O-benzyl-2-deoxy-D-xylofuranose 
• 95990-82-2 1-O-Methyl-3,5-di-O-benzyl-2-deoxy-D-xylofuranose 
• 203730-19-2 ((3R,4S,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-(4-methoxy-benzyl)-amine 
• 203730-24-9 (3R,4S)-3,4-Bis-benzyloxy-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 203730-21-6 (3R,4S)-3,4-Bis-benzyloxy-1-(4-methoxy-benzyl)-pyrrolidin-2-one 
• 203730-22-7 (3R,4S)-3,4-bis(benzyloxy)pyrrolidin-2-one 
• 16838-89-4 2,3,5-tri-O-benzyl-D-xylofuranose 
• 210548-17-7 2-benzoyl-3,5-dibenzyl-D-xylose dibenzyl dithioacetal 

Relevant articles and documents

Stereoselective 1,4-phenyl migration from silicon to carbon in α-siloxy cyclic acetal systems: A concise synthesis of 1,2-cis-phenyl C-glycoside and enantioenriched silanol

The treatment of O-glycoside with alcohol in the presence of montmorillonite K10 clay and 4-? MS yields the 1,4-aryl migration product with a 1,2-cis-phenyl C-glycoside scaffold and a chiral silyl moiety with high stereoselectivity.

Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-α-D-ribofuranose and -β-D-lyxofuranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-D-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and -β-D-talopyranose

The title compounds 5-O-acetyl-1,2-anhydro-3-O-benzyl-α-D-ribofuranose and 5-O-acetyl-1,2-anhydro-3-O-benzyl-β-D-lyxofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-β-D-talopyranose, and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-β-D-mannofuranose and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-D-mannofuranose have each been synthesized from the corresponding 2-O-tosylate and 1-free hydroxyl intermediates by base-initiated intramolecular SN2 ring closure in almost quantitative yields. Acetyl and benzoyl groups were not affected in the ring closure reactions. Condensation of 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-β-D-mannofuranose with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose in the presence of ZnCl2 as the catalyst afforded the 1,2-trans-linked 6-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose and 5-O-acetyl-3,6-di-O-benzyl-α-D-mannofuranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose as the sole products in satisfactory yields, while condensation of 5-O-acetyl-1,2-anhydro-3-O-benzyl-β-D-lyxofuranose with 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose yielded the 1,2-trans-linked 5-O-acetyl-3-O-benzyl-α-D-lyxofuranosyl-(1 → 5)-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose as the sole product in a good yield. The 6-O-acetyl group in the glycosyl donor, 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose, did not influence the stereoselectivity of the ring-opening-coupling reaction.

Synthesis and antiviral evaluation of 2'-deoxy-4'-thio-L-nucleosides and their phosphotriester derivatives bearing S-acyl-2-thioethyl bioreversible phosphate-protecting groups

A new route to 2-deoxy-4-thio-L-ribofuranose and the synthesis of some 4'-thio-L-nucleosides are reported. Also, the bis(SATE) phosphotriester derivatives of 2'-deoxy-4'-thio-L-cytidine and -adenosine were synthesized and their biological activities are discussed.

Novel asymmetric synthesis of an indolizidine alkaloid, (+)-lentiginosine employing highly stereoselective hydrogenation of α-hydroxypyrrolidine

An efficient and novel process is described for the asymmetric synthesis of a (1S,2S,8aS)-dihydroxyindolizidine alkaloid, (+)-lentiginosine in which the asymmetric deoxygenation of the quaternary α-hydroxypyrrolidine derivative derived from D-xylose is used as a key step.