(2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol

Base Information

• Chemical Name: (2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol
• CAS No.: 176301-78-3
• Molecular Formula: C₂₈H₃₄O₂S₂Si
• Molecular Weight: 494.794
• Mol file: 176301-78-3.mol

Synonyms:(2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol

Chemical Property of (2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol

There total 11 articles about (2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-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:

4-Nitro-benzoic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester (176214-58-7) → (2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol (176301-78-3)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/0040-4039(96)00139-6

Reference yield:

L-arabinose dibenzyl dithioacetal (40733-11-7) → (2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol (176301-78-3)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂SO₄, CuSO₄

2: 1.) t-BuOK, 2.) LiAlH₄ / 1.) THF, DMSO, 2.) THF

3: 68 percent / DIAD, PPh₃ / tetrahydrofuran

4: Dowex H(+) / methanol

5: DMAP, imidazole / CH₂Cl₂

6: DMAP / CH₂Cl₂

7: 67 percent / NaI, Et₃N / butan-2-one

8: NaOMe / methanol

With 1H-imidazole; dmap; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; Dowex H(+); sulfuric acid; potassium tert-butylate; sodium methylate; copper(II) sulfate; triethylamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; butanone;

DOI:10.1016/0040-4039(96)00139-6

Reference yield:

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside (134938-97-9) → (2R,3S)-5-Benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol (176301-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1: TiCl₄ / CH₂Cl₂

2: DMAP, imidazole / CH₂Cl₂

With 1H-imidazole; dmap; titanium tetrachloride; In dichloromethane;

DOI:10.1016/0040-4039(96)00138-4

upstream raw materials:

(2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol

tert-butylchlorodiphenylsilane

4-Nitro-benzoic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

L-arabinose dibenzyl dithioacetal