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

Base Information

• Chemical Name: methyl 2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propenoate
• CAS No.: 367523-33-9
• Molecular Formula: C₃₀H₄₉NO₆Si₂
• Molecular Weight: 575.893
• Mol file: 367523-33-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

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

Reference yield:

(4-bromophenyl)magnesium bromide (18620-02-5) → 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:

Multi-step reaction with 2 steps

1: 30 percent / PdCl₂(CH₃CN)2; dppf / tetrahydrofuran / 20 °C

2: 80 percent / Pd(OAc)2; PPh₃; NEt₃ / dimethylformamide / 12 h / 100 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; dichloro bis(acetonitrile) palladium(II); triethylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Grignard reaction / 2: Heck reaction;

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

Reference yield:

p-tert-butylphenyl 4,6-di-O-tert-butyl(dimethyl)silyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (201232-73-7) → 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:

Multi-step reaction with 2 steps

1: 30 percent / PdCl₂(CH₃CN)2; dppf / tetrahydrofuran / 20 °C

2: 80 percent / Pd(OAc)2; PPh₃; NEt₃ / dimethylformamide / 12 h / 100 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; dichloro bis(acetonitrile) palladium(II); triethylamine; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Grignard reaction / 2: Heck reaction;

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

upstream raw materials:

Methyl 2-acetamidoacrylate

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

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