(2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane

Base Information

• Chemical Name: (2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane
• CAS No.: 732276-05-0
• Molecular Formula: C₄₄H₅₇NO₉SSi
• Molecular Weight: 804.089
• Mol file: 732276-05-0.mol

Synonyms:(2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane

Chemical Property of (2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane

There total 4 articles about (2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane 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:

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate (114185-07-8) → (2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane (732276-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide / 3 h / 0 - 20 °C

2.1: 35.39 g / LiBH₄ / diethyl ether; methanol / 3 h / 0 °C

3.1: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.33 h / -70 °C

4.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -70 °C

4.2: 83 percent / tetrahydrofuran; hexane / 4 h / -70 °C

With 1H-imidazole; lithium borohydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation;

DOI:10.1021/jo0496291

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane (732276-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide / 3 h / 0 - 20 °C

2.1: 35.39 g / LiBH₄ / diethyl ether; methanol / 3 h / 0 °C

3.1: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.33 h / -70 °C

4.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -70 °C

4.2: 83 percent / tetrahydrofuran; hexane / 4 h / -70 °C

With 1H-imidazole; lithium borohydride; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation;

DOI:10.1021/jo0496291

Reference yield:

(2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol (658052-78-9) → (2R,5R,6S)-3-benzenesulfonyl-1-benzyloxy-5-tert-butyldiphenylsilyloxy-2-tert-butoxycarbonylamino-4-hydroxy-6,7-O-isopropylidene-6,7-dihydroxyheptane (732276-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.33 h / -70 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -70 °C

2.2: 83 percent / tetrahydrofuran; hexane / 4 h / -70 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation;

DOI:10.1021/jo0496291

upstream raw materials:

ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate

tert-butylchlorodiphenylsilane

(2S,3S)-2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanol

(2R,3S)-ethyl 2-O-tert-butyldiphenylsilyloxy-3,4-O-isopropylidene-3,4-dihydroxybutanoate