o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside
• CAS No.: 467219-66-5
• Molecular Formula: C₃₇H₃₈O₈S
• Molecular Weight: 642.77
• Mol file: 467219-66-5.mol

Synonyms:o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside

Chemical Property of o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside

There total 7 articles about o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 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:

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (382141-78-8) → o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside (467219-66-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / NaOMe / methanol / 3 h / 20 °C

2: 85 percent / Et₃N; DMAP / pyridine / 8 h / 20 °C

3: 92 percent / NaH / dimethylformamide / 12 h / 20 °C

4: TBAF / tetrahydrofuran / 12 h / 20 °C

5: pyridine / 7 h

With pyridine; dmap; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; triethylamine; In tetrahydrofuran; pyridine; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00093-9

Reference yield:

2-(methoxycarbonyl)phenyl 1-thio-β-D-galactopyranoside (382141-84-6) → o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside (467219-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / Et₃N; DMAP / pyridine / 8 h / 20 °C

2: 92 percent / NaH / dimethylformamide / 12 h / 20 °C

3: TBAF / tetrahydrofuran / 12 h / 20 °C

4: pyridine / 7 h

With pyridine; dmap; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00093-9

Reference yield:

o-methoxycarbonylphenyl 6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-galactopyranoside (467219-68-7) → o-methoxycarbonylphenyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside (467219-66-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / NaH / dimethylformamide / 12 h / 20 °C

2: TBAF / tetrahydrofuran / 12 h / 20 °C

3: pyridine / 7 h

With pyridine; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(02)00093-9

upstream raw materials:

acetic anhydride

2-((2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-ylsulfanyl)-benzoic acid methyl ester

2-(methoxycarbonyl)phenyl 1-thio-β-D-galactopyranoside

(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

p-aminophenyl (α-D-galacopyranosyl)-(1->3)-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

p-N-acryloylamidophenyl (α-D-galacopyranosyl)-(1->3)-β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside

(2R,3R,4S,5R,6R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

p-nitrophenyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-galactopyranosyl)-(1->3)-2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside