(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol

Base Information

• Chemical Name: (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol
• CAS No.: 827043-48-1
• Molecular Formula: C₂₇H₃₀O₈
• Molecular Weight: 482.53

Synonyms:(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol

Chemical Property of (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol

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Technology Process of (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol

There total 2 articles about (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol 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: 95.0%

benzoyl chloride (98-88-4) + (1R,2R,3S)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-5-(hydroxymethyl)-4-cyclohexene-1,2,3-triol (827043-47-0) → (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol (827043-48-1)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 12h;

DOI:10.1021/ja0470158

Reference yield:

(2S,3S,4aS,8aR)-7-Hydroxymethyl-2,3-dimethoxy-2,3-dimethyl-2,3,8,8a-tetrahydro-4aH-benzo[1,4]dioxin-5-one → (1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol (827043-48-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / DIBAL-H / tetrahydrofuran; hexane / 5 h / 0 °C

2: 95 percent / DMAP; pyridine / 12 h / 20 °C

With pyridine; dmap; diisobutylaluminium hydride; In tetrahydrofuran; hexane;

DOI:10.1021/ja0470158

Reference yield: 94.0%

(1R,2R,3S)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3-triol (827043-48-1) → (1R,2S,3S,4R,5R)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3,4,5-pentol (827043-49-2)

Guidance literature:

With ruthenium trichloride; sodium periodate; In ethyl acetate; acetonitrile; at 0 ℃; for 0.05h;

DOI:10.1021/ja0470158

upstream raw materials:

benzoyl chloride

(1R,2R,3S)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-5-(hydroxymethyl)-4-cyclohexene-1,2,3-triol

Downstream raw materials:

(1R,2S,3S,4R,5R)-3-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3,4,5-pentol

bis[(1S,2S,3S,4R)-2,3,4-trihydroxy-5-(hydroxymethyl)-5-cyclohexenyl]amine

(1R,2S,3R,4R)-3,4-di-O-benzoyl-5-(benzyloxymethyl)-5-cyclohexene-1,2,3,4-tetraol

(1R,2S,3R,4R)-3,4-di-O-benzoyl-5-(benzyloxymethyl)-1,2-[(2S,3S)-2,3-dimethoxybutan-2,3-dioxy]-4-cyclohexene-1,2,3,4-tetraol

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