methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside

Base Information

• Chemical Name: methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside
• CAS No.: 86030-94-6
• Molecular Formula: C₂₃H₃₂O₄Si
• Molecular Weight: 400.59
• Mol file: 86030-94-6.mol

Synonyms:methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside

Chemical Property of methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside

There total 17 articles about methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside 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: 90.0%

methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-α-D-erythro-hexopyranoside (86030-95-7) → methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside (86030-94-6)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 48h; Ambient temperature;

DOI:10.1021/jo00206a010

Reference yield: 64.0%

(3R,5S)-3-tert-butyldiphenylsilyloxy-5,6-(isopropylidenedioxy)hexanal (915201-16-0) + trimethyl orthoformate (149-73-5) → methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside (86030-94-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; at 70 ℃;

DOI:10.1002/chir.20782

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-β-D-erythro-hexopyranoside (86030-94-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 94.1 percent / imidazole / dimethylformamide / 20 °C

2.1: DIBALH / diethyl ether; toluene / 0.25 h / -78 °C

2.2: 77.2 percent / diethyl ether; toluene; methanol / -78 - 20 °C

3.1: pTsOH*Py / methanol / 1 h / Heating

3.2: 63.7 percent / pTsOH / methanol / 20 °C

With 1H-imidazole; diisobutylaluminium hydride; In methanol; diethyl ether; N,N-dimethyl-formamide; toluene;

DOI:10.1002/ejoc.200600849

upstream raw materials:

methyl 3-O-(tert-butyldiphenylsilyl)-2,4-dideoxy-α-D-erythro-hexopyranoside

tert-Butyl-((2S,4R,6S)-2-methoxy-6-trityloxymethyl-tetrahydro-pyran-4-yloxy)-diphenyl-silane

(3R,5S)-3-tert-butyldiphenylsilyloxy-5,6-(isopropylidenedioxy)hexanal

trimethyl orthoformate

Downstream raw materials:

(2S,4R,6R)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-carbaldehyde

tert-Butyl-((2S,4R,6R)-2-iodomethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-diphenyl-silane

(2S,4R,6S)-2-(p-chlorobenzenesulfonyloxy)methyl-4-tert-butyldiphenylsilyloxy-6-methoxytetrahydropyran

(4R,6R)-(+)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one