[(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-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: [(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester
• CAS No.: 134694-97-6
• Molecular Formula: C₃₉H₅₈N₂O₁₁Si₃
• Molecular Weight: 815.153

Synonyms:[(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester

Chemical Property of [(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-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:

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Technology Process of [(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester

There total 5 articles about [(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-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: 81.0%

tert.-butylhydroperoxide (75-91-2) + [(2R,4aR,5R,6R,7R,8S,8aS,9aS,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4,4a,6,8-tetrakis-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-2H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester (145958-18-5) → [(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester (134694-97-6) + [(2R,4aR,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-tert-butoxy-2-methyl-4,4a,6,8-tetrakis-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-2H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester

Guidance literature:

With copper dichloride; In water; acetonitrile; at 28 - 33 ℃; for 1h;

DOI:10.1021/jo00055a021

Reference yield: 81.0%

[(2R,4aR,5R,6R,7R,8S,8aS,9aS,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4,4a,6,8-tetrakis-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-2H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester (145958-18-5) → [(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester (134694-97-6) + [(2R,4aR,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-tert-butoxy-2-methyl-4,4a,6,8-tetrakis-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-2H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester

Guidance literature:

With tert.-butylhydroperoxide; copper dichloride; In water; acetonitrile; at 28 - 33 ℃; for 1h;

DOI:10.1021/jo00055a021

Reference yield:

1,3-bis(N-benzyloxycarbonyl)-spectinomycin (56733-83-6) → [(4aS,5R,6R,7R,8S,8aS,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4-oxo-4a,6,8-tris-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-4H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester (134694-97-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 103 g / triethylamine / acetonitrile / 3 h / 50 °C

2: 81 percent / copper(II) chloride*2 H₂O / acetonitrile; H₂O / 1 h / 28 - 33 °C

With triethylamine; copper dichloride; In water; acetonitrile;

DOI:10.1021/jo00055a021

upstream raw materials:

tert.-butylhydroperoxide

[(2R,4aR,5R,6R,7R,8S,8aS,9aS,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-2-methyl-4,4a,6,8-tetrakis-trimethylsilanyloxy-4a,5,6,7,8,8a,9a,10a-octahydro-2H-1,9,10-trioxa-anthracen-7-yl]-methyl-carbamic acid benzyl ester

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

benzyl chloroformate

Downstream raw materials:

[(4aR,5S,6S,7R,8S,8aR,9aR,10aR)-5-(Benzyloxycarbonyl-methyl-amino)-4a,6,8-trihydroxy-2-methyl-4-oxo-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-but-3-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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