Phenyl 3-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside triacetate

Base Information

• Chemical Name: Phenyl 3-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside triacetate
• CAS No.: 158198-55-1
• Molecular Formula: C25H28O8S
• Molecular Weight: 488.559
• Mol file: 158198-55-1.mol

Synonyms:Phenyl 3-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside triacetate

Chemical Property of Phenyl 3-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside triacetate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl 3-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside triacetate

There total 6 articles about Phenyl 3-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside triacetate 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: 88.0%

thiophenol (108-98-5) + 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9) → phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside (158198-55-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo962300y

Reference yield: 10.0%

phenylthiotrimethylsilane (4551-15-9) + 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9) → phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside (158198-55-1) + phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-α-D-glucopyranoside

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 0 ℃; for 4h;

DOI:10.1016/0008-6215(95)00257-X

Reference yield:

benzyl-O-β-D-glucopyranoside (97590-76-6) → phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside (158198-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate / 6 h / 110 °C

2: 63 percent / Et₂O*BF₃ / CH₂Cl₂ / 20 °C

With boron trifluoride diethyl etherate; sodium acetate; In dichloromethane;

DOI:10.1081/SCC-120027259

upstream raw materials:

phenylthiotrimethylsilane

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

thiophenol

benzyl-O-β-D-glucopyranoside

Downstream raw materials:

methyl (cyclohexyl 3-O-benzyl-β-D-glucopyranosyluronate)

methyl (benzyl 3-O-benzyl-β-D-glucopyranosyluronate)

p-methoxyphenyl 2-amino-6-O-benzyl-2-N,3-O-carbonyl-2-deoxy-4-O-(methyl 3-Obenzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)-β-D-glucopyranoside

methyl 2,3,4-tri-O-acetyl-6-O-(methyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyluronate)-α-D-glucopyranoside