methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Base Information

• Chemical Name: methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate
• CAS No.: 1387509-48-9
• Molecular Formula: C₄₇H₅₅NO₁₇S
• Molecular Weight: 938.016

Synonyms:methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Chemical Property of methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

Chemical Property:

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Useful:

Technology Process of methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

There total 4 articles about methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate 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: 67.0%

methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside (1387509-35-4) + methyl [dibutylphosphoryl (5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-D-glycero-α-L-altro-non-2-ulopyranosid)onate] → methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate (1387509-48-9)

Guidance literature:

methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside; methyl [dibutylphosphoryl (5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-D-glycero-α-L-altro-non-2-ulopyranosid)onate]; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 1.25h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol301779e

Reference yield:

methyl 2,3,6-tri-O-benzyl-4-deoxy-4-trifluoromethanesulfonyl-α-D-glucopyranoside (87871-03-2) → methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate (1387509-48-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2.1: hydrazine hydrate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

3.1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

3.2: 1.25 h / -78 °C / Inert atmosphere

With hydrazine hydrate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol301779e

Reference yield:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate (1387509-48-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 1.5 h / -78 °C / Inert atmosphere

2.1: N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: hydrazine hydrate / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

4.2: 1.25 h / -78 °C / Inert atmosphere

With sodium hexamethyldisilazane; hydrazine hydrate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol301779e

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-deoxy-4-trifluoromethanesulfonyl-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-S-acetyl-4-thio-α-D-galactopyranoside

Downstream raw materials:

methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate

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