(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol
• CAS No.: 175877-47-1
• Molecular Formula: C₂₄H₃₂O₄Si
• Molecular Weight: 412.601
• Mol file: 175877-47-1.mol

Synonyms:(2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol

Chemical Property of (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol

There total 2 articles about (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-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: 72.0%

ethyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (23339-15-3) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol (175877-47-1)

Guidance literature:

With triethylamine; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1080/07328309708006546

Reference yield:

ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside (3323-72-6) → (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol (175877-47-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 2 h / 25 °C

2: 72 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

With sodium methylate; triethylamine; In methanol; dichloromethane;

DOI:10.1080/07328309708006546

Reference yield: 94.0%

methyl chloroformate (79-22-1) + (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol (175877-47-1) → ethyl 6-O-(tert-butyldiphenylsilyl)-4-O-methoxycarbonyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (162934-16-9)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1080/07328309708006546

upstream raw materials:

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

tert-butylchlorodiphenylsilane

ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

Downstream raw materials:

ethyl 6-O-(tert-butyldiphenylsilyl)-4-O-methoxycarbonyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

ethyl 6-O-tert-butyldiphenylsilyl-4-O-methoxycarbonyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside

(2R,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol