ethyl 2,4-di-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: ethyl 2,4-di-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 1246814-18-5
• Molecular Formula: C₂₂H₂₈O₅S
• Molecular Weight: 404.527
• Mol file: 1246814-18-5.mol

Synonyms:ethyl 2,4-di-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of ethyl 2,4-di-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2,4-di-O-benzyl-1-thio-β-D-glucopyranoside

There total 4 articles about ethyl 2,4-di-O-benzyl-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: 89.0%

ethyl 2,4-di-O-benzyl-3,6-di-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside → ethyl 2,4-di-O-benzyl-1-thio-β-D-glucopyranoside (1246814-18-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 2h;

DOI:10.1002/chem.202002401

Reference yield: 75.0%

ethyl 3,6-di-O-allyl-2,4-di-O-benzyl-1-thio-β-D-glucopyranoside (1246814-17-4) → ethyl 2,4-di-O-benzyl-1-thio-β-D-glucopyranoside (1246814-18-5)

Guidance literature:

ethyl 3,6-di-O-allyl-2,4-di-O-benzyl-1-thio-β-D-glucopyranoside; With potassium tert-butylate; In dimethyl sulfoxide; at 20 - 100 ℃; for 0.333333h; Inert atmosphere;

With hydrogenchloride; In water; acetone; at 60 ℃; for 2h;

DOI:10.1021/jo1014189

Reference yield:

ethyl 1-thio-β-D-glucopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → ethyl 2,4-di-O-benzyl-1-thio-β-D-glucopyranoside (1246814-18-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 20 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 °C

3: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

With 1H-imidazole; sodium hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/chem.202002401

upstream raw materials:

ethyl 3,6-di-O-allyl-2,4-di-O-benzyl-1-thio-β-D-glucopyranoside

ethyl 3,6-di-O-(tert-butyldimethylsilyl)-1-thio-β-d-glucopyranoside

ethyl 1-thio-β-D-glucopyranoside

Downstream raw materials:

ethyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-β-D-glucopyranoside

Refernces

• 1、 Yang, Weizhun,Sun, Jiansong,Lu, Wenxiang,Li, Yan,Shan, Lei,Han, Wei,Zhang, Wei-Dong,Yu, Biao. "Synthesis of kaempferol 3- O -(3″,6″-Di- O - E - p -coumaroyl)-β- D -glucopyranoside, efficient glycosylation of flavonol 3-OH with glycosyl o -alkynylbenzoates as donors". experimental part. p. 6879 - 6888. Retrieved 2010/11/24.