1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene

Base Information

• Chemical Name: 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene
• CAS No.: 367523-29-3
• Molecular Formula: C₂₄H₄₁BrO₃Si₂
• Molecular Weight: 513.663
• Mol file: 367523-29-3.mol

Synonyms:1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene

Chemical Property of 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene

There total 1 articles about 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene 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: 30.0%

(4-bromophenyl)magnesium bromide (18620-02-5) + p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (201232-73-7) → 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene (367523-29-3)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4020(02)00831-1

Reference yield: 82.0%

methyl vinyl ketone (78-94-4,25038-87-3) + 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene (367523-29-3) → 4-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]-2-oxobut-3-ene

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100 ℃; for 12h;

DOI:10.1016/S0040-4020(02)00831-1

Reference yield: 80.0%

Methyl 2-acetamidoacrylate (35356-70-8) + 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene (367523-29-3) → methyl 2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propenoate (367523-33-9)

Guidance literature:

With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; at 100 ℃; for 12h;

DOI:10.1016/S0040-4020(02)00831-1

upstream raw materials:

(4-bromophenyl)magnesium bromide

p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

Downstream raw materials:

methyl 2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propenoate

methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate