ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
• CAS No.: 209113-61-1
• Molecular Formula: C₄₅H₄₆O₁₄S
• Molecular Weight: 842.918
• Mol file: 209113-61-1.mol

Synonyms:ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

There total 2 articles about ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 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: 92.0%

ethyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (35784-51-1) + ethyl 2,3-di-O-acetyl-3-C-(benzyloxymethyl)-1-thio-α/β-D-erythrofuranoside (209113-60-0) → ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (209113-61-1)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid;

DOI:10.1016/S0040-4039(98)00673-X

Reference yield:

1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside (245432-69-3) → ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (209113-61-1)

Guidance literature:

Multi-step reaction with 2 steps

1: SnCl₄

2: 92 percent / NIS, triflic acid

With N-iodo-succinimide; trifluorormethanesulfonic acid; tin(IV) chloride;

DOI:10.1016/S0040-4039(98)00673-X

Reference yield: 89.0%

ethyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside (209113-61-1) → C43H42O15

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane;

DOI:10.1016/S0040-4039(98)00673-X

upstream raw materials:

ethyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside

ethyl 2,3-di-O-acetyl-3-C-(benzyloxymethyl)-1-thio-α/β-D-erythrofuranoside

1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside

Downstream raw materials:

3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

3,4,5-trimethoxyphenyl 6-O-(5-O-benzyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside

6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate

3,4,5-trimethoxyphenyl 6-O-(2,3-di-O-acetyl-5-O-benzyl-β-D-erythro-apiofuranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranoside