Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester
• CAS No.: 883743-18-8
• Molecular Formula: C₁₇H₂₂O₈S
• Molecular Weight: 386.423

Synonyms:Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

Chemical Property of Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

There total 2 articles about Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-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: 96.0%

4-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-β-D-fructopyranose (883743-17-7) → Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester (883743-18-8)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃;

DOI:10.1016/j.tet.2005.12.023

Reference yield:

3-O-benzoyl-4-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-β-D-fructopyranose (340969-78-0) → Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester (883743-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / NaOMe / methanol

2: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

With sodium methylate; Dess-Martin periodane; In methanol; dichloromethane; 2: Dess-Martin oxidation;

DOI:10.1016/j.tet.2005.12.023

Reference yield: 76.0%

Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester (883743-18-8) → 4-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-β-D-psicopyranose (883743-19-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃;

DOI:10.1016/j.tet.2005.12.023

upstream raw materials:

4-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-β-D-fructopyranose

3-O-benzoyl-4-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-β-D-fructopyranose

Downstream raw materials:

4-O-benzyl-1,2-O-isopropylidene-5-O-methanesulfonyl-β-D-psicopyranose

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-L-tagatopyranose

(2R,3S,4R,5S)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)pyrrolidine

5-azido-3,4-di-O-benzyl-5-deoxy-α-L-tagatopyranose

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