Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester
• CAS No.: 478693-74-2
• Molecular Formula: C₁₇H₂₆O₉S₂
• Molecular Weight: 438.52

Synonyms:Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester

Chemical Property of Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester

There total 2 articles about Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-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:

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside (68907-47-1) → Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester (478693-74-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / Et₃SiH; TFA / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 154.0 mg / pyridine; DMAP / 7 h / -10 - 20 °C

With pyridine; triethylsilane; dmap; trifluoroacetic acid; In dichloromethane;

DOI:10.1055/s-2002-34380

Reference yield:

methanesulfonyl chloride (124-63-0) + methyl 6-O-benzyl-2-deoxy-2-C-methyl-α-D-altropyranoside (478693-62-8) → Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester (478693-74-2)

Guidance literature:

With pyridine; dmap; at -10 - 20 ℃; for 7h;

DOI:10.1055/s-2002-34380

Reference yield: 95.0%

Methanesulfonic acid (2R,3R,4S,5S,6S)-2-benzyloxymethyl-3-methanesulfonyloxy-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester (478693-74-2) → methyl 2,3,4-trideoxy-2-C-methyl-6-O-benzyl α-D-threo-hex-3-enopyranoside (142041-83-6)

Guidance literature:

With sodium iodide; zinc; In N,N-dimethyl-formamide; for 24h; Heating;

DOI:10.1055/s-2002-34380

upstream raw materials:

methanesulfonyl chloride

methyl 6-O-benzyl-2-deoxy-2-C-methyl-α-D-altropyranoside

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

Downstream raw materials:

methyl 2,3,4-trideoxy-2-C-methyl-6-O-benzyl α-D-threo-hex-3-enopyranoside

(2S,5S,6S)-6-Methoxy-5-methyl-tetrahydro-pyran-2-carbaldehyde

methyl 2-C-methyl-2,3,4-trideoxy-α-D-threo-hexopyranoside

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