methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

Base Information

Chemical Name:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate
CAS No.:286939-02-4
Molecular Formula:C₅₅H₆₅NO₁₉
Molecular Weight:1044.12
Hs Code.:

methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

Synonyms:methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

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Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

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Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

There total 2 articles about methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate 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,3R,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-(4-methoxy-phenoxy)-tetrahydro-pyran-4-yl]-methanol

: 286939-02-4
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: SmI₂ / 0.25 h / 20 °C

With samarium diiodide; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Swern oxidation / 2: Condensation;
DOI:10.1021/jo990564p

Reference yield:

: 121512-93-4
[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone

: 247027-84-5
p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-(formyl)-β-D-galacto-hexopyranoside

: 286939-02-4
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

: 286939-03-5
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(S)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

Guidance literature:: With samarium diiodide; at 20 ℃; for 0.25h;
DOI:10.1021/jo990564p

Reference yield:

: 286939-02-4
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

: 247027-87-8
methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; water; ethyl acetate; at 20 ℃; for 24h;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1805::AID-EJOC1805<3.0.CO;2-A