(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one
• CAS No.: 129778-50-3
• Molecular Formula: C₂₇H₃₀O₃SSi
• Molecular Weight: 462.685
• Mol file: 129778-50-3.mol

Synonyms:(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one

Chemical Property of (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one

There total 7 articles about (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one 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:

(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan (125440-13-3) + benzenesulfenyl chloride (931-59-9) → (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one (129778-55-8) + (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one (129778-50-3)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00033a004

Reference yield:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) → (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one (129778-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1. LiN(TMS)2 / 1. -78 deg C, THF; 2. -78 deg C to r.t.

2: TMSOTf / CH₂Cl₂ / a.) -78 deg C, 3 h; b.) r.t., 1 h

With trimethylsilyl trifluoromethanesulfonate; lithium hexamethyldisilazane; In dichloromethane;

DOI:10.1021/jo00033a004

Reference yield:

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one (102717-29-3) + diphenyldisulfane (882-33-7) → (3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one (129778-55-8) + (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-dihydro-furan-2-one (129778-50-3)

Guidance literature:

With lithium cyclohexylisopropylamide; Yield given. Multistep reaction. Yields of byproduct given; THF, -20 deg C;

DOI:10.1246/cl.1990.1459

upstream raw materials:

N-(phenylthio)-ε-caprolactam

(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-trimethylsilanyloxy-2,3-dihydro-furan

6,6-Dimethyl-1-phenylsulfanyl-piperidin-2-one

Downstream raw materials:

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylsulfanyl-tetrahydro-furan-2-ol

1-O-acetyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-D-erythro-pentofuranose

1-<5-O-tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-α-D-erythro-pentofuranosyl>thymine

1-<5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-2-phenylthio-β-D-erythro-pentofuranosyl>thymine