methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside
• CAS No.: 220864-58-4
• Molecular Formula: C₂₉H₃₀Br₂O₅
• Molecular Weight: 618.362

Synonyms:methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside

Chemical Property:

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Technology Process of methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside

There total 2 articles about methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside 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: 87.0%

carbon tetrabromide (558-13-4) + methyl 2,3,4-tri-O-benzyl-β-D-galacto-hexodialdo-1,5-pyranoside (117305-40-5) → methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside (220864-58-4)

Guidance literature:

With triphenylphosphine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/(sici)1099-0690(199902)1999:2<471::aid-ejoc471>3.0.co;2-2

Reference yield:

methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside (40653-32-5,641635-63-4) → methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside (220864-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -40 - 20 °C

2: 81 percent / PPh₃; Et₃N / CH₂Cl₂ / 0 - 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In dichloromethane; 1: Oxidation / 2: dibromomethylenation;

DOI:10.1021/jo0005619

Reference yield: 67.0%

methyl 2,3,4-tri-O-benzyl-7,7-dibromo-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside (220864-58-4) → methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside (306765-57-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo0005619

upstream raw materials:

carbon tetrabromide

methyl 2,3,4-tri-O-benzyl-β-D-galacto-hexodialdo-1,5-pyranoside

methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-galacto-hept-6-ynopyranoside

6-C-(2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-β-D-glycero-L-manno-heptitol-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-D-galactono-1,5-lactone

methyl 6-C-(2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-β-D-glycero-L-manno-heptitol-1-yl)-2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranoside

methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-7-C-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-galacto-hept-6-ynopyranoside

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