1,3,4,6-Tetra-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-a-L-fucopyranosyl)-D-galactopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-a-L-fucopyranosyl)-D-galactopyranose
• CAS No.: 141990-06-9
• Molecular Formula: C₄₁H₄₂O₁₇
• Molecular Weight: 806.774
• Mol file: 141990-06-9.mol

Synonyms:1,3,4,6-Tetra-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-a-L-fucopyranosyl)-D-galactopyranose

Chemical Property of 1,3,4,6-Tetra-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-a-L-fucopyranosyl)-D-galactopyranose

Chemical Property:

• PSA: 211.79000
• LogP: 3.50770
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

99%min ^*data from raw suppliers

1,3,4,6-Tetra-O-acetyl-2-(2’,3’,4’-tri-O-benzoyl-α-L-fucopyranosyl)-galactopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,3,4,6-Tetra-O-acetyl-2-(2’,3’,4’-tri-O-benzoyl-α-L-fucopyranosyl)-galactopyranose (cas# 141990-06-9) is a compound useful in organic synthesis.

Technology Process of 1,3,4,6-Tetra-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-a-L-fucopyranosyl)-D-galactopyranose

There total 5 articles about 1,3,4,6-Tetra-O-acetyl-2-O-(2,3,4-tri-O-benzoyl-a-L-fucopyranosyl)-D-galactopyranose 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: 97.0%

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide (14218-08-7,41881-44-1,53297-33-9,60820-93-1,61198-82-1,67986-91-8,73068-86-7,131897-72-8,131897-73-9) + 1,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (19186-40-4) → O-(2,3,4-Tri-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-1,3,4,6-tetra-O-acetyl-α-D-galactopyranose (139760-07-9,141990-06-9)

Guidance literature:

With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate; In dichloromethane; for 0.25h;

DOI:10.1021/jo00034a047

Reference yield: 85.0%

1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose (92418-39-8) + 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate (161007-95-0) → 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose (573700-74-0,141990-06-9)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/S0008-6215(03)00004-1

Reference yield:

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate (161007-95-0) → C41H42O17 (141990-06-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

1.2: 1 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

2.1: palladium dichloride / methanol; dichloromethane / 1 h / 20 °C

3.1: pyridine / 10 h / 0 - 20 °C / Inert atmosphere

With palladium dichloride; In pyridine; methanol; dichloromethane;

DOI:10.1021/acs.joc.0c00442

upstream raw materials:

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide

1,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

1,3,4,6-tetra-O-acetyl-α,β-D-glucopyranose

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate

Downstream raw materials:

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide

ophiopogonin C

Refernces

• 1、 Zou, Chuan-Chun,Hou, Shu-Jie,Shi, Yang,Lei, Ping-Sheng,Liang, Xiao-Tian. "The synthesis of gracillin and dioscin: Two typical representatives of spirostanol glycosides". . p. 721 - 727. Retrieved 2007/10/03.