benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside

Base Information

• Chemical Name: benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside
• CAS No.: 683773-15-1
• Molecular Formula: C₃₇H₅₂O₁₈
• Molecular Weight: 784.809
• Mol file: 683773-15-1.mol

Synonyms:benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside

Chemical Property of benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside

There total 5 articles about benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside 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: 42.0%

benzyl 2,4-di-O-acetyl-α-L-rhamnopyranoside (683773-14-0) + 4-pentenyl 3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-β-L-fucopyranoside (683773-13-9) → benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside (683773-15-1)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jo030304e

Reference yield:

(2R,3R,4R,5R,6S)-2-benzyloxy-tetrahydro-6-methyl-2H-pyran-3,4,5-triol (3359-35-1,16741-29-0,71731-74-3,78120-06-6,84911-79-5,84911-80-8,87598-99-0,87599-00-6,88818-92-2,97133-57-8,114298-06-5,127000-09-3) → benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside (683773-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-toluenesulfonic acid monohydrate / dimethylformamide / 2 h / 50 °C

1.2: 79 percent / pyridine / 20 °C

2.1: 42 percent / NIS; TMSOTf / CH₂Cl₂; diethyl ether / 4 h / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo030304e

Reference yield:

Acetic acid (2S,3R,4R,5S,6S)-4-acetoxy-5-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (136737-89-8) → benzyl 2,4-di-O-acetyl-3-O-[3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-α-L-fucopyranosyl]-α-L-rhamnopyranoside (683773-15-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / -78 - 20 °C

2: 42 percent / NIS; TMSOTf / CH₂Cl₂; diethyl ether / 4 h / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; dichloromethane;

DOI:10.1021/jo030304e

upstream raw materials:

benzyl 2,4-di-O-acetyl-α-L-rhamnopyranoside

4-pentenyl 3-O-acetyl-4-O-(2,3-di-O-acetyl-4-O-methyl-α-L-rhamnopyranosyl)-2-O-methyl-β-L-fucopyranoside

(2R,3R,4R,5R,6S)-2-benzyloxy-tetrahydro-6-methyl-2H-pyran-3,4,5-triol

Acetic acid (2S,3R,4R,5S,6S)-4-acetoxy-5-methoxy-6-methyl-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester