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

Base Information

• Chemical Name: Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 183001-82-3
• Molecular Formula: C₁₆H₂₁BrO₈S
• Molecular Weight: 453.308

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

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

Chemical Property:

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

There total 2 articles about Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-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: 80.0%

methyl 4,6-O-benzylidene-3-O-methanesulfonyl-2-O-methyl-α-D-altropyranoside (183182-16-3) → Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester (183001-82-3)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 2h; Heating;

DOI:10.1016/0957-4166(96)00330-8

Reference yield:

methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-altropyranoside (74410-55-2) → Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester (183001-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / pyridine / 24 h / Ambient temperature

2: 80 percent / NBS, BaCO₃ / CCl₄ / 2 h / Heating

With pyridine; N-Bromosuccinimide; barium carbonate; In tetrachloromethane;

DOI:10.1016/0957-4166(96)00330-8

Reference yield: 100.0%

Benzoic acid (2S,3R,4R,5S,6S)-2-bromomethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester (183001-82-3) + potassium thioacetate (10387-40-3) → Benzoic acid (2S,3R,4R,5S,6S)-2-acetylsulfanylmethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester (183001-83-4)

Guidance literature:

In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/0957-4166(96)00330-8

upstream raw materials:

methyl 4,6-O-benzylidene-3-O-methanesulfonyl-2-O-methyl-α-D-altropyranoside

methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-altropyranoside

Downstream raw materials:

Benzoic acid (2S,3R,4R,5S,6S)-2-acetylsulfanylmethyl-4-methanesulfonyloxy-5,6-dimethoxy-tetrahydro-pyran-3-yl ester

(3S,4R,5R)-4-Benzyloxy-5-((R)-2-hydroxy-1-methoxy-ethyl)-tetrahydro-thiophen-3-ol

(R)-((2S,3R,4S)-3-Benzyloxy-4-hydroxy-tetrahydro-thiophen-2-yl)-methoxy-acetaldehyde

methyl 4-O-benzyl-2-O-methyl-3,6-thioanhydro-α-D-mannopyranoside

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