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

Base Information

Chemical Name:methyl (5-amino-7,8,9-tri-O-acetyl-5,4-N,O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate-(2->6)-(methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside)
CAS No.:1235555-39-1
Molecular Formula:C₄₅H₅₃NO₁₇
Molecular Weight:879.912
Hs Code.:

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

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

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

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

There total 7 articles about methyl (5-amino-7,8,9-tri-O-acetyl-5,4-N,O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate-(2->6)-(methyl 2,3,4-tri-O-benzyl-α-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: 95.0%

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 1235555-29-9
methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: 1235555-39-1
methyl (5-amino-7,8,9-tri-O-acetyl-5,4-N,O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate-(2->6)-(methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside)

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; acetonitrile; at -78 - -50 ℃; for 1.16667h; diastereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1021/jo100824s

Reference yield:

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 1235555-29-9
methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate

: 1235555-39-1
methyl (5-amino-7,8,9-tri-O-acetyl-5,4-N,O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate-(2->6)-(methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside)

: C₄₅H₅₃NO₁₇

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -40 ℃; for 2h; Overall yield = 100 percent; stereoselective reaction; Molecular sieve;
DOI:10.1002/ejoc.202100718

Reference yield:

: 1071226-27-1
methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate

: 1235555-39-1
methyl (5-amino-7,8,9-tri-O-acetyl-5,4-N,O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate-(2->6)-(methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside)

: C₄₅H₅₃NO₁₇

Guidance literature:: Multi-step reaction with 4 steps

1: methanesulfonic acid / methanol / 70 °C / Inert atmosphere

2: sodium hydrogencarbonate / acetonitrile; water / 3 h / 0 °C

3: pyridine / 12 h / 20 °C

4: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 2 h / -40 °C / Molecular sieve

With pyridine; N-iodo-succinimide; methanesulfonic acid; trifluorormethanesulfonic acid; sodium hydrogencarbonate; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1002/ejoc.202100718