isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside

Base Information

• Chemical Name: isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside
• CAS No.: 909710-51-6
• Molecular Formula: C₂₇H₃₈O₃Si
• Molecular Weight: 438.682
• Mol file: 909710-51-6.mol

Synonyms:isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside

Chemical Property of isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside

There total 6 articles about isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside 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: 80.0%

isopropyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-methylsulphonyl-α-D-erythro-hex-2-enopyranoside (909710-49-2) + ethylmagnesium bromide (925-90-6) → isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside (909710-51-6)

Guidance literature:

ethylmagnesium bromide; With CuCN; In tetrahydrofuran; at -40 ℃; for 0.0833333h;

isopropyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-methylsulphonyl-α-D-erythro-hex-2-enopyranoside; In tetrahydrofuran; at -40 - -18 ℃;

DOI:10.1080/07328300600735090

Reference yield: 80.0%

isopropyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-methylsulphonyl-α-D-erythro-hex-2-enopyranoside (909710-49-2) + diethylzinc (557-20-0) → isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside (909710-51-6)

Guidance literature:

diethylzinc; With CuCN; In tetrahydrofuran; at 0 ℃; for 0.166667h;

isopropyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-methylsulphonyl-α-D-erythro-hex-2-enopyranoside; In tetrahydrofuran; at 0 ℃; for 0.333333h;

DOI:10.1080/07328300600735090

Reference yield:

isopropyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (23339-26-6,56196-34-0) → isopropyl 4-C-ethyl-6-O-tert-butyldiphenylsilyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranoside (909710-51-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 90 percent / imidazole / dimethylformamide / 2 h / 0 °C

2.1: 84 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

3.1: CuCN / tetrahydrofuran / 0.08 h / -40 °C

3.2: 80 percent / tetrahydrofuran / -40 - -18 °C

With 1H-imidazole; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/07328300600735090

upstream raw materials:

isopropyl 6-O-tert-butyldiphenylsilyl-2,3-dideoxy-4-O-methylsulphonyl-α-D-erythro-hex-2-enopyranoside

ethylmagnesium bromide

diethylzinc

isopropyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside