Benzoyl-carbamic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

Base Information

• Chemical Name: Benzoyl-carbamic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester
• CAS No.: 176301-76-1
• Molecular Formula: C₃₆H₃₉NO₄S₂Si
• Molecular Weight: 641.927
• Mol file: 176301-76-1.mol

Synonyms:

Chemical Property of Benzoyl-carbamic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoyl-carbamic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

There total 11 articles about Benzoyl-carbamic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester 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:

L-arabinose dibenzyl dithioacetal (40733-11-7) → Benzoyl-carbamic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester (176301-76-1)

Guidance literature:

Multi-step reaction with 9 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

9: toluene

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; toluene; 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) → Benzoyl-carbamic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester (176301-76-1)

Guidance literature:

Multi-step reaction with 3 steps

1: TiCl₄ / CH₂Cl₂

2: DMAP, imidazole / CH₂Cl₂

3: 85 percent / toluene

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

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

Reference yield:

(2R,3S)-5-(benzylthio)-2-(hydroxymethyl)tetrahydrothiophen-3-ol (134700-25-7) → Benzoyl-carbamic acid (2R,3S)-5-benzylsulfanyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester (176301-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1: DMAP, imidazole / CH₂Cl₂

2: 85 percent / toluene

With 1H-imidazole; dmap; In dichloromethane; toluene;

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

upstream raw materials:

L-arabinose dibenzyl dithioacetal

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside

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

tert-butylchlorodiphenylsilane