Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester

Base Information

• Chemical Name: Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester
• CAS No.: 113886-52-5
• Molecular Formula: C₃₅H₄₄N₄O₁₃
• Molecular Weight: 728.753

Synonyms:

Chemical Property of Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester

There total 2 articles about Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-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:

[(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,4R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (113886-44-5,113973-81-2,113973-84-5,113974-86-0,113974-88-2) → Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester (113886-52-5,113973-82-3,113973-83-4,113974-87-1)

Guidance literature:

Multi-step reaction with 2 steps

1: d-10-camphorsulfonic acid / dimethylformamide

2: NaOAc

With camphor-10-sulfonic acid; sodium acetate; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.35.2136

Reference yield:

acetic anhydride (108-24-7) + {(3aS,4R,5S,7R)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-hydroxy-2,2-dimethyl-7-nitro-hexahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester → Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester (113886-52-5,113973-82-3,113973-83-4,113974-87-1)

Guidance literature:

With sodium acetate; Yield given;

DOI:10.1248/cpb.35.2136

Reference yield: 56.0%

Acetic acid (4R,6S,7R,7aS)-7-[(2R,3R,6S)-6-(acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-6-benzyloxycarbonylamino-2,2-dimethyl-4-nitro-hexahydro-benzo[1,3]dioxol-5-yl ester (113886-52-5,113973-82-3,113973-83-4,113974-87-1) → {(3aS,4R,5S,7R,7aR)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-2,2-dimethyl-7-nitro-hexahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester (113886-45-6,113973-80-1) + {(3aS,4R,5S,7R,7aS)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-2,2-dimethyl-7-nitro-hexahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester (113886-45-6,113973-80-1)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 5 ℃; for 0.5h;

DOI:10.1248/cpb.35.2136

upstream raw materials:

acetic anhydride

[(2R,3R,6S)-6-(Acetylamino-methyl)-2-((1R,2S,4R,6R)-2-benzyloxycarbonylamino-3,5,6-trihydroxy-4-nitro-cyclohexyloxy)-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Downstream raw materials:

{(3aS,4R,5S,7R,7aR)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-2,2-dimethyl-7-nitro-hexahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

{(3aS,4R,5S,7R,7aS)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-benzyloxycarbonylamino-tetrahydro-pyran-2-yloxy]-2,2-dimethyl-7-nitro-hexahydro-benzo[1,3]dioxol-5-yl}-carbamic acid benzyl ester

dibecacin

{(1R,2S,3R,4R,5S)-4-[(2R,3R,6S)-6-(Acetylamino-methyl)-3-ethoxycarbonylamino-tetrahydro-pyran-2-yloxy]-5-ethoxycarbonylamino-2,3-dihydroxy-cyclohexyl}-carbamic acid ethyl ester

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