(2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol
• CAS No.: 511274-40-1
• Molecular Formula: C₁₄H₂₀O₅S
• Molecular Weight: 300.376

Synonyms:(2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Chemical Property of (2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Chemical Property:

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Technology Process of (2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol

There total 1 articles about (2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol 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: 97.0%

phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-β-D-glucopyranose (161391-28-2) → (2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol (511274-40-1)

Guidance literature:

With (1S)-10-camphorsulfonic acid; In methanol; at 20 ℃; for 48h;

DOI:10.1021/jo051021k

Reference yield: 90.0%

(2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol (511274-40-1) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-hydroxy-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester (870537-88-5)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo051021k

Reference yield: 83.0%

(2R,3R,4S,5R,6S)-2-Hydroxymethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol (511274-40-1) + pent-4-enoyl chloride (39716-58-0) → Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester (511274-60-5)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jo051021k

upstream raw materials:

phenyl 4,6-O-benzylidene-2,3-di-O-methyl-1-thio-β-D-glucopyranose

Downstream raw materials:

Pent-4-enoic acid (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-pent-4-enoyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-yl ester

(2S,3R,4S,5R,6R)-3,4-Dimethoxy-5-pent-4-enyloxy-6-pent-4-enyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran

Toluene-4-sulfonic acid (2R,3R,4S,5R,6S)-3-hydroxy-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

(2R,3R,4S,5R,6S)-2-Aminomethyl-4,5-dimethoxy-6-phenylsulfanyl-tetrahydro-pyran-3-ol

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