Benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-bromomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-bromomethyl-6-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 116013-30-0
• Molecular Formula: C₁₈H₂₁BrO₈
• Molecular Weight: 445.264

Synonyms:Benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-bromomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-bromomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-bromomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

There total 5 articles about Benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-bromomethyl-6-methoxy-tetrahydro-pyran-3-yl ester 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%

methyl-4,6-O-benzylidene-2,3-diacetyl-α-D-glucopyranoside (4141-45-1) → methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside (18929-80-1,73139-31-8,81823-21-4,116013-29-7,116013-30-0,116013-31-1,56543-19-2)

Guidance literature:

DOI:10.1016/S0008-6215(00)88060-X

Reference yield: 90.0%

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranoside (72813-11-7) → Benzoic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-bromomethyl-6-methoxy-tetrahydro-pyran-3-yl ester (116013-30-0)

Guidance literature:

With Bromotrichloromethane; In tetrachloromethane; for 1.5h; Irradiation;

DOI:10.1039/c39880000094

Reference yield: 24.0%

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside (2774-22-3,4141-45-1,6748-84-1,6752-75-6,15451-81-7,20750-01-0,35311-30-9,56687-82-2,59121-47-0,72813-11-7,76333-82-9,112968-15-7,130464-34-5) → methyl 2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-glucopyranoside (18929-80-1,73139-31-8,81823-21-4,116013-29-7,116013-30-0,116013-31-1,56543-19-2) + methyl 2,3-di-O-acetyl-6-O-benzoyl-α-D-glucopyranoside (29868-43-7) + methyl 2,3-di-O-acetyl-4-O-benzoyl-α-D-glucopyranoside (56543-18-1)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1002/ejoc.201200299

upstream raw materials:

methyl-4,6-O-benzylidene-2,3-diacetyl-α-D-glucopyranoside

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glalactopyranoside

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranoside

Downstream raw materials:

methyl (methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-α-D-gluco-heptopyranosid)uronate

methyl 6-deoxy-β-D-galactopyranoside

methyl 2,3-di-O-acetyl-4-O-benzoyl-6-deoxy-β-D-galactopyranoside

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