Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester
• CAS No.: 125608-47-1
• Molecular Formula: C₃₄H₃₃BrO₆
• Molecular Weight: 617.536

Synonyms:Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester

There total 3 articles about Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-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: 90.0%

(2S,3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran → Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester (125608-47-1)

Guidance literature:

With bromine; In dichloromethane; at 0 ℃; in the dark;

DOI:10.1039/c39890001124

Reference yield:

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) (125392-62-3) → Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester (125608-47-1)

Guidance literature:

With bromine; at 0 ℃;

DOI:10.1021/ja00070a048

Reference yield:

ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (132360-46-4) → Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran-3-yl ester (125608-47-1)

Guidance literature:

With bromine; In dichloromethane; for 0.5h;

DOI:10.1021/jo0508595

upstream raw materials:

3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate)

ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-α-D-thiomannopyranoside

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