1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate

Base Information

• Chemical Name: 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate
• CAS No.: 82079-38-7
• Molecular Formula: C₁₉H₂₆O₇S
• Molecular Weight: 398.477

Synonyms:1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate

Chemical Property of 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate

Chemical Property:

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Technology Process of 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate

There total 6 articles about 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate 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: 87.0%

4-methylbenzenesulfinyl chloride (10439-23-3) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-p-toluenesulfinate (79378-71-5,79378-73-7,82079-38-7,82079-39-8) + 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate (82079-38-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at -78 ℃; Yields of byproduct given;

DOI:10.1021/jo00051a022

Reference yield: 87.0%

4-methylbenzenesulfinyl chloride (10439-23-3) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-p-toluenesulfinate (79378-71-5,79378-73-7,82079-38-7,82079-39-8) + 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate (82079-38-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at -78 ℃; Yields of byproduct given;

DOI:10.1021/jo00051a022

Reference yield: 30.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-p-toluenesulfinate (79378-71-5,79378-73-7,82079-38-7,82079-39-8) + 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate (82079-38-7)

Guidance literature:

With pyridine; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 1h; Yield given; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(99)00066-X

upstream raw materials:

4-methylbenzenesulfinyl chloride

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

2,4,6-triisopropylphenylsulfonyl chloride

Downstream raw materials:

(+)-(R)-ethyl p-tolyl sulfoxide

(+)-(S)-allyl-p-toluenesulphinamide

(S)-1-(ethylsulfinyl)-4-methylbenzene

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