(3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane

Base Information

• Chemical Name: (3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane
• CAS No.: 943032-33-5
• Molecular Formula: C₂₆H₃₅NO₅
• Molecular Weight: 441.568

Synonyms:(3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane

Chemical Property of (3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane

Chemical Property:

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Technology Process of (3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane

There total 2 articles about (3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane 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:

(1S,4R,5R)-1-O-benzyl-4,5-O-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]-1,4,5-trihydroxy-2-cyclohexene → (3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane (943032-33-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 83 percent / NaIO₄ / RuCl₃ / ethyl acetate; acetonitrile; aq. phosphate buffer / 0.17 h / 0 °C / pH 7

2.1: NaIO₄ / methanol

2.2: aq. NaHCO₃ / ethyl acetate

3.1: NaBH(OAc)3 / CH₂Cl₂ / 20 °C

With sodium periodate; sodium tris(acetoxy)borohydride; ruthenium trichloride; In methanol; phosphate buffer; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/jo070058x

Reference yield:

C19H28O7 (943032-32-4) → (3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane (943032-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaIO₄ / methanol

1.2: aq. NaHCO₃ / ethyl acetate

2.1: NaBH(OAc)3 / CH₂Cl₂ / 20 °C

With sodium periodate; sodium tris(acetoxy)borohydride; In methanol; dichloromethane;

DOI:10.1021/jo070058x

Reference yield: 99.0%

(3R,4R,6S)-1-benzyl-6-O-benzyl-3,4,6-trihydroxy-3,4-[(2S,3S)-2,3-dimethoxybutane-2,3-dioxy]azepane (943032-33-5) → (3R,4R,6S)-3,4,6-trihydroxyazepane (284031-41-0,284031-35-2,312489-60-4)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jo070058x

upstream raw materials:

C₁₉H₂₈O₇

Downstream raw materials:

(3R,4R,6S)-3,4,6-trihydroxyazepane

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