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

Base Information

• Chemical Name: methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate
• CAS No.: 493009-57-7
• Molecular Formula: C₃₀H₅₁NO₆Si₂
• Molecular Weight: 577.909
• Mol file: 493009-57-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate 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: 64.0%

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) → methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate (493009-57-7)

Guidance literature:

With (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate; hydrogen; at 20 ℃; for 24h; under 3750.3 - 7500.6 Torr;

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

Reference yield:

Methyl 2-acetamidoacrylate (35356-70-8) → methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate (493009-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Pd(OAc)2; PPh₃; NEt₃ / dimethylformamide / 12 h / 100 °C

2: 64 percent / [Rh(COD)(S,S)-(Et-DuPHOS)]OTf; H₂ / 24 h / 20 °C / 3750.3 - 7500.6 Torr

With palladium diacetate; (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate; hydrogen; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide; 1: Heck reaction;

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

Reference yield:

(4-bromophenyl)magnesium bromide (18620-02-5) → methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate (493009-57-7)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 64 percent / [Rh(COD)(S,S)-(Et-DuPHOS)]OTf; H₂ / 24 h / 20 °C / 3750.3 - 7500.6 Torr

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; dichloro bis(acetonitrile) palladium(II); (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate; hydrogen; 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-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propenoate

Methyl 2-acetamidoacrylate

(4-bromophenyl)magnesium bromide

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