benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside

Base Information

• Chemical Name: benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside
• CAS No.: 848842-23-9
• Molecular Formula: C₂₀H₂₆O₇
• Molecular Weight: 378.422
• Mol file: 848842-23-9.mol

Synonyms:benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside

Chemical Property of benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside

There total 3 articles about benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2-propenyl)-α-D-lyxofuranoside (848842-22-8) → benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside (848842-23-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside (158780-52-0) → benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside (848842-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 11 mg / pyridine

2: 87 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

With pyridine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/j.tetasy.2004.12.001

Reference yield:

(3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester (158780-50-8) → benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-epoxypropyl)-α-D-lyxofuranoside (848842-23-9)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium hydride / tetrahydrofuran / 1 h / Heating

2: 11 mg / pyridine

3: 87 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

With pyridine; lithium aluminium tetrahydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2004.12.001

upstream raw materials:

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2-propenyl)-α-D-lyxofuranoside

phenylmethyl 2,3-O-(1-methylethylidene)-4-C-(prop-2-enyl)-α-D-lyxofuranoside

(3aR,4S,6S,6aS)-4-Allyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester

Downstream raw materials:

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2-acetyloxy-3-phenylthiopropyl)-α-D-lyxofuranoside

benzyl 5-O-acetyl-2,3-O-isopropylidene-4-C-(2,3-diacetyloxy-3-phenylthiopropyl)-α-D-lyxofuranoside