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

Base Information

• Chemical Name: 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
• CAS No.: 85951-30-0
• Molecular Formula: C₃₅H₄₁N₃O₁₂
• Molecular Weight: 695.723

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 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

There total 4 articles about 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 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:

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,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 (85951-30-0)

Guidance literature:

Multi-step reaction with 3 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

3: dimethylformamide / 8 h / 55 °C

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

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

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,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 (85951-30-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: dimethylformamide / 8 h / 55 °C

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In tetrachloromethane; N,N-dimethyl-formamide;

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

Reference yield:

1,3-bis(N-benzyloxycarbonyl)-spectinomycin (56733-83-6) → 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 (85951-30-0)

Guidance literature:

Multi-step reaction with 4 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

4: dimethylformamide / 8 h / 55 °C

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

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

upstream raw materials:

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

N,N-dimethyl-formamide dimethyl acetal

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

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

Downstream raw materials:

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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