[(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

Base Information

• Chemical Name: [(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
• CAS No.: 103198-47-6
• Molecular Formula: C₃₃H₃₈N₂O₁₁
• Molecular Weight: 638.672

Synonyms:

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 7 articles about [(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 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:

[(4aR,5R,6S,7S,8S,8aR,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-((E)-but-1-enyl)-4a,8-dihydroxy-4-oxo-6-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester → [(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 (103198-47-6)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 0 ℃; for 5h; Yield given;

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) → [(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 (103198-47-6)

Guidance literature:

Multi-step reaction with 6 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

4: hexamethyldisilazane / 2.5 h / 55 °C

5: 0 - 25 °C

6: 48percent aqueous HF / acetonitrile / 5 h / 0 °C

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

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

Reference yield:

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) → [(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 (103198-47-6)

Guidance literature:

Multi-step reaction with 4 steps

1: dimethylformamide / 8 h / 55 °C

2: hexamethyldisilazane / 2.5 h / 55 °C

3: 0 - 25 °C

4: 48percent aqueous HF / acetonitrile / 5 h / 0 °C

With hydrogen fluoride; 1,1,1,3,3,3-hexamethyl-disilazane; In N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

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 (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

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

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

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