methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside

Base Information

• Chemical Name: methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside
• CAS No.: 89160-10-1
• Molecular Formula: C₂₉H₃₀Br₂O₅
• Molecular Weight: 618.362

Synonyms:methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside

Chemical Property of methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside

Chemical Property:

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Technology Process of methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside

There total 2 articles about methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside 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: 69.0%

carbon tetrabromide (558-13-4) + methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside (89160-10-1)

Guidance literature:

With triethylamine; triphenylphosphine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo0005619

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (210834-15-4,641635-63-4) → methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside (89160-10-1)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 69 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: 93.0%

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + methyl 7,7-dibromo-6,7-dideoxy-2,3,4-tri-O-benzyl-α-D-gluco-hept-6-enopyranoside (89160-10-1) → (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylethynyl)-tetrahydro-pyran-2-ol

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -50 ℃;

DOI:10.1002/(SICI)1099-0690(199905)1999:5<1185::AID-EJOC1185>3.0.CO;2-A

upstream raw materials:

carbon tetrabromide

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

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

Downstream raw materials:

(2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-prop-1-ynyl-tetrahydro-pyran

methyl-2,3,4-tri-O-benzyl-6,7-dideoxy-6,6,7,7-tetradehydro-α-D-glucoheptopyranoside

(3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-prop-1-ynyl-tetrahydro-pyran-2-one

Acetic acid (3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-prop-1-ynyl-tetrahydro-pyran-2-yl ester

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