(2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol

Base Information

• Chemical Name: (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS No.: 556039-06-6
• Molecular Formula: C₂₆H₃₆O₆SSi
• Molecular Weight: 504.72
• Mol file: 556039-06-6.mol

Synonyms:(2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol

Chemical Property of (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol

There total 6 articles about (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol 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: 99.0%

tert-butyldimethylsilyl chloride (18162-48-6) + phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside (273749-60-3) → (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol (556039-06-6)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 25h; Inert atmosphere;

DOI:10.1021/jacs.0c01774

Reference yield:

β-D-glucose (492-61-5) → (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol (556039-06-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine

1.2: 90 percent / BF₃*Et₂O

2.1: 100 percent / MeONa / methanol

3.1: 94 percent / imidazole

With 1H-imidazole; sodium methylate; In pyridine; methanol;

DOI:10.1007/s007060200016

Reference yield:

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside (13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1) → (2R,4aR,6S,7R,8R,8aR)-8-tert-butyldimethylsilyloxy-2-(4-methoxyphenyl)-6-phenylthiohexahydropyrano[3,2-d][1,3]dioxin-7-ol (556039-06-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / MeONa / methanol

2: 94 percent / imidazole

With 1H-imidazole; sodium methylate; In methanol;

DOI:10.1007/s007060200016

upstream raw materials:

tert-butyldimethylsilyl chloride

phenyl 4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranoside

β-D-glucose

phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside

Downstream raw materials:

phenyl 2-O-allyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside

phenyl 2-O-allyl-3-O-^tbutyldimethylsilyl-4,6-O-p-methoxybenzylidene-1-thio-β-D-glucopyranoside