4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose

Base Information

• Chemical Name: 4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose
• CAS No.: 1075748-91-2
• Molecular Formula: C₃₈H₄₄O₄Si₂
• Molecular Weight: 620.936
• Mol file: 1075748-91-2.mol

Synonyms:4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose

Chemical Property of 4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose

There total 3 articles about 4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose 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: 81.0%

(2R,3R)-3-hydroxy-2-(hydroxymethyl)-2H-pyran-4(3H)-one (14125-64-5) + tert-butylchlorodiphenylsilane (58479-61-1) → 4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose (1075748-91-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/jo801596q

Reference yield:

D-glucal triacetate (2873-29-2) → 4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose (1075748-91-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium methylate / methanol

2: dipyridinium dichromate / acetic acid; ethyl acetate

3: 1H-imidazole / N,N-dimethyl-formamide

With 1H-imidazole; dipyridinium dichromate; sodium methylate; In methanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo401032r

Reference yield:

D-glucal (13265-84-4) → 4,6-di-O-tert-butyldiphenylsilyl-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose (1075748-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1: dipyridinium dichromate / acetic acid; ethyl acetate

2: 1H-imidazole / N,N-dimethyl-formamide

With 1H-imidazole; dipyridinium dichromate; In acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo401032r

upstream raw materials:

(2R,3R)-3-hydroxy-2-(hydroxymethyl)-2H-pyran-4(3H)-one

tert-butylchlorodiphenylsilane

D-glucal triacetate

D-glucal

Downstream raw materials:

C₃₈H₄₆O₄Si₂