Acetic acid (4aS,5S,6R,7R,8S,8aS,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-yl ester

Base Information

• Chemical Name: Acetic acid (4aS,5S,6R,7R,8S,8aS,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-yl ester
• CAS No.: 88625-85-8
• Molecular Formula: C₃₄H₃₆N₂O₁₄
• Molecular Weight: 696.665

Synonyms:

Chemical Property of Acetic acid (4aS,5S,6R,7R,8S,8aS,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (4aS,5S,6R,7R,8S,8aS,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-yl ester

There total 3 articles about Acetic acid (4aS,5S,6R,7R,8S,8aS,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-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:

Acetic acid (2R,4aR,5S,6R,7R,8S,8aS,9aS,10aR)-4-acetoxy-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-5,6,7,8,8a,10a-hexahydro-2H-1,9,10-trioxa-anthracen-4a-yl ester (88625-84-7) → Acetic acid (4aS,5S,6R,7R,8S,8aS,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-yl ester (88625-85-8)

Guidance literature:

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In tetrachloromethane; for 0.333333h; Ambient temperature; Irradiation;

DOI:10.1016/S0040-4039(00)99493-0

Reference yield:

Formic acid (2R,4aR,5S,6R,7R,8S,8aS,9aS,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6-formyloxy-4a-hydroxy-2-methyl-4-oxo-decahydro-1,9,10-trioxa-anthracen-8-yl ester (88625-83-6) → Acetic acid (4aS,5S,6R,7R,8S,8aS,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-yl ester (88625-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / pyridine, dimethylaminopyridine / ethyl acetate / 10 h / 55 °C

2: 1,3-dibromo-5,5-dimethyl hydantoin / CCl₄ / 0.33 h / Ambient temperature; Irradiation

With pyridine; dmap; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In tetrachloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)99493-0

Reference yield:

1,3-bis(N-benzyloxycarbonyl)-spectinomycin (56733-83-6) → Acetic acid (4aS,5S,6R,7R,8S,8aS,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-yl ester (88625-85-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / acetic anhydride, pyridine / ethyl acetate / 1) from -40 deg C to 25 deg C; 2) 25 deg C, 16 hrs

2: 77 percent / pyridine, dimethylaminopyridine / ethyl acetate / 10 h / 55 °C

3: 1,3-dibromo-5,5-dimethyl hydantoin / CCl₄ / 0.33 h / Ambient temperature; Irradiation

With pyridine; dmap; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; acetic anhydride; In tetrachloromethane; ethyl acetate;

DOI:10.1016/S0040-4039(00)99493-0

upstream raw materials:

Acetic acid (2R,4aR,5S,6R,7R,8S,8aS,9aS,10aR)-4-acetoxy-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6,8-diformyloxy-2-methyl-5,6,7,8,8a,10a-hexahydro-2H-1,9,10-trioxa-anthracen-4a-yl ester

Formic acid (2R,4aR,5S,6R,7R,8S,8aS,9aS,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-6-formyloxy-4a-hydroxy-2-methyl-4-oxo-decahydro-1,9,10-trioxa-anthracen-8-yl ester

1,3-bis(N-benzyloxycarbonyl)-spectinomycin

Downstream raw materials:

Acetic acid (4aS,5S,6S,7R,8S,8aR,9aR,10aR)-5,7-bis-(benzyloxycarbonyl-methyl-amino)-2-((E)-2-dimethylamino-vinyl)-6,8-dihydroxy-4-oxo-5,6,7,8,8a,10a-hexahydro-4H-1,9,10-trioxa-anthracen-4a-yl ester

Trospectomycin

[(4aR,5S,6S,7R,8S,8aR,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-((E)-but-1-enyl)-4a,6,8-trihydroxy-4-oxo-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester

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