Methanesulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 13225-28-0
• Molecular Formula: C₂₂H₂₇IO₇S
• Molecular Weight: 562.423

Synonyms:Methanesulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Methanesulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester

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

2,3-Di-O-benzyl-4,6-di-O-methyl-sulfonyl-methyl-α-D-glucopyranosid (13225-27-9) → Methanesulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester (13225-28-0)

Guidance literature:

With sodium iodide; In butanone; Heating;

DOI:10.1055/s-1999-2709

Reference yield:

→ 6-Jod-2,3-di-O-benzyl-6-desoxy-4-O-methylsulfonyl-methyl-α-D-glucopyranosid (13225-28-0,55570-14-4)

Guidance literature:

2,3-Di-O-benzyl-4,6-di-O-methylsulfonyl-α-methyl-D-glucopyranosid, NaI in sd. Methylaethylketon;

DOI:10.1021/ja01068a037

Reference yield: 83.0%

Methanesulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yl ester (13225-28-0) → methyl 2,3-di-O-benzyl-6-deoxy-4-O-mesyl-α-D-xylohex-5-enopyranoside (99322-17-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

upstream raw materials:

2,3-Di-O-benzyl-4,6-di-O-methyl-sulfonyl-methyl-α-D-glucopyranosid

Downstream raw materials:

methyl 2,3-di-O-benzyl-6-deoxy-4-O-mesyl-α-D-xylohex-5-enopyranoside

Methanesulfonic acid (1S,2S,3R,4R,5S)-3,4-bis-benzyloxy-1-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester

Methanesulfonic acid (2S,3S,4R,5R,6S)-4,5-bis-benzyloxy-2-hydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester

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