ethylthio 3-O-benzyl-2,3-dideoxy-2,4-di-C-methyl-6-O-t-butyldiphenylsilyl-α,β-D-gulopyranoside

Base Information

• Chemical Name: ethylthio 3-O-benzyl-2,3-dideoxy-2,4-di-C-methyl-6-O-t-butyldiphenylsilyl-α,β-D-gulopyranoside
• CAS No.: 92232-46-7
• Molecular Formula: C₃₃H₄₄O₃SSi
• Molecular Weight: 548.862
• Mol file: 92232-46-7.mol

Synonyms:

Chemical Property of ethylthio 3-O-benzyl-2,3-dideoxy-2,4-di-C-methyl-6-O-t-butyldiphenylsilyl-α,β-D-gulopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethylthio 3-O-benzyl-2,3-dideoxy-2,4-di-C-methyl-6-O-t-butyldiphenylsilyl-α,β-D-gulopyranoside

There total 3 articles about ethylthio 3-O-benzyl-2,3-dideoxy-2,4-di-C-methyl-6-O-t-butyldiphenylsilyl-α,β-D-gulopyranoside 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: 94.0%

methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside (82707-04-8) + ethanethiol (75-08-1) → ethylthio 3-O-benzyl-2,3-dideoxy-2,4-di-C-methyl-6-O-t-butyldiphenylsilyl-α,β-D-gulopyranoside (92232-46-7,92232-52-5)

Guidance literature:

With zinc(II) chloride; at -25 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)82415-7

Reference yield:

benzyl bromide (100-39-0) → ethylthio 3-O-benzyl-2,3-dideoxy-2,4-di-C-methyl-6-O-t-butyldiphenylsilyl-α,β-D-gulopyranoside (92232-46-7,92232-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.98 g / NaH / 0 °C

2: 94 percent / ZnCl₂ / 0.5 h / -25 °C

With sodium hydride; zinc(II) chloride;

DOI:10.1016/S0040-4020(01)82415-7

Reference yield:

(2S,4R,5R,6S)-2-Hydroxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-4-ol (82731-53-1,92215-57-1,118360-78-4,118360-79-5) → ethylthio 3-O-benzyl-2,3-dideoxy-2,4-di-C-methyl-6-O-t-butyldiphenylsilyl-α,β-D-gulopyranoside (92232-46-7,92232-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.98 g / NaH / 0 °C

2: 94 percent / ZnCl₂ / 0.5 h / -25 °C

With sodium hydride; zinc(II) chloride;

DOI:10.1016/S0040-4020(01)82415-7

upstream raw materials:

methyl 3-O-benzyl-6-O-t-butyldiphenylsilyl 2,4-dideoxy-2,4-di-C-methyl-α-D-gulopyranoside

ethanethiol

benzyl bromide

(2S,4R,5R,6S)-2-Hydroxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-4-ol

Downstream raw materials:

(3R,4R,5R,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3,5-dimethyl-tetrahydro-pyran-2-ol

3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-5-O-methylsulfonyl-1-O-triphenylmethyl-D-gulitol

5,6-anhydro-3-O-benzyl-2,4-dideoxy-2,4-di-C-methyl-1-O-triphenylmethyl-L-galactitol