(3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol

Base Information

• Chemical Name: (3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol
• CAS No.: 488097-20-7
• Molecular Formula: C₃₉H₄₃N₃O₇
• Molecular Weight: 665.786
• Mol file: 488097-20-7.mol

Synonyms:(3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol

Chemical Property of (3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol

There total 13 articles about (3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol 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: 91.0%

(3S,4S)-1-benzenesulfonyl-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol (488097-19-4) → (3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol (488097-20-7)

Guidance literature:

With tetraethylammonium bromide; phenol; for 8h; Electrochemical reaction;

DOI:10.1021/jo0206521

Reference yield:

9-bromo-9-phenyl-9H-fluorene (55135-66-5) → (3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol (488097-20-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: K₃PO₄; Pb(NO₃)2 / acetonitrile / 36 h / 20 °C

1.2: 16.26 g / hydrochloric acid / methanol; H₂O / 1 h / Heating

2.1: 76 percent / pyridine / 14 h / 65 °C

3.1: 72 percent / KHMDS / tetrahydrofuran / 2 h / -20 - 3 °C

4.1: 97 percent / LiAlH₄ / tetrahydrofuran / 0.33 h

5.1: oxalyl chloride; DMSO / CH₂Cl₂ / 3 h / -78 °C

5.2: 94 percent / triethylamine / CH₂Cl₂ / 0.17 h / -78 °C

6.1: 93 percent / p-toluenesulfonic acid / tetrahydrofuran; ethanol / 5 h / 20 °C

7.1: Triton B / dimethylsulfoxide; methanol / 20 °C

7.2: 97 percent / dimethylsulfoxide; methanol / 1.5 h / 65 °C

8.1: 77 percent / tert-butyl hydroperoxide; Triton B / tetrahydrofuran; methanol / 0.33 h / 20 °C

9.1: 90 percent / H₂; pyridine / 10percent Pd/C / methanol / 84 h / 3102.97 Torr

10.1: tetrahydrofuran / 0.33 h / 0 - 20 °C

10.2: 80 percent / NaBH₄ / ethanol / 22 h / 20 °C

11.1: 91 percent / tetraethylammonium bromide; phenol / 8 h / Electrochemical reaction

With pyridine; tert.-butylhydroperoxide; potassium phosphate; lithium aluminium tetrahydride; lead(II) nitrate; oxalyl dichloride; tetraethylammonium bromide; hydrogen; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; phenol; 10percent Pd/C; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 5.1: Swern oxidation;

DOI:10.1021/jo0206521

Reference yield:

3-((S)-3-Amino-2-hydroxy-3-methoxycarbonyl-propylamino)-5-methoxymethoxy-4-methyl-benzoic acid methyl ester → (3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol (488097-20-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: K₃PO₄; Pb(NO₃)2 / acetonitrile / 36 h / 20 °C

1.2: 16.26 g / hydrochloric acid / methanol; H₂O / 1 h / Heating

2.1: 76 percent / pyridine / 14 h / 65 °C

3.1: 72 percent / KHMDS / tetrahydrofuran / 2 h / -20 - 3 °C

4.1: 97 percent / LiAlH₄ / tetrahydrofuran / 0.33 h

5.1: oxalyl chloride; DMSO / CH₂Cl₂ / 3 h / -78 °C

5.2: 94 percent / triethylamine / CH₂Cl₂ / 0.17 h / -78 °C

6.1: 93 percent / p-toluenesulfonic acid / tetrahydrofuran; ethanol / 5 h / 20 °C

7.1: Triton B / dimethylsulfoxide; methanol / 20 °C

7.2: 97 percent / dimethylsulfoxide; methanol / 1.5 h / 65 °C

8.1: 77 percent / tert-butyl hydroperoxide; Triton B / tetrahydrofuran; methanol / 0.33 h / 20 °C

9.1: 90 percent / H₂; pyridine / 10percent Pd/C / methanol / 84 h / 3102.97 Torr

10.1: tetrahydrofuran / 0.33 h / 0 - 20 °C

10.2: 80 percent / NaBH₄ / ethanol / 22 h / 20 °C

11.1: 91 percent / tetraethylammonium bromide; phenol / 8 h / Electrochemical reaction

With pyridine; tert.-butylhydroperoxide; potassium phosphate; lithium aluminium tetrahydride; lead(II) nitrate; oxalyl dichloride; tetraethylammonium bromide; hydrogen; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; phenol; 10percent Pd/C; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 5.1: Swern oxidation;

DOI:10.1021/jo0206521

upstream raw materials:

(3S,4S)-1-benzenesulfonyl-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocin-5-ol

9-bromo-9-phenyl-9H-fluorene

methyl (2S,3S)-3-[N-[1-benzenesulfonyl-4-methoxy-4-oxo-(2,3)-[N-(9-phenylfluoren-9-yl)aziridino]butyl]amino]-5-methoxymethoxy-4-methylbenzoate

(3S,4S)-1-benzenesulfonyl-7-methoxymethoxy-5-oxo-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-1,2,3,4,5,6-hexahydrobenzo[b]azocine-9-carbaldehyde

Downstream raw materials:

(3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-5-hydroxy-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-3,4,5,6-tetrahydro-2H-benzo[b]azocin-1-yl acetate

(3S,4S)-6-carbamoyloxymethyl-9-diethoxymethyl-7-methoxymethoxy-5-oxo-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-3,4,5,6-tetrahydro-2H-benzo[b]azocin-1-yl acetate

carbamic acid 5-diethoxymethyl-3,9-dihydroxy-7-methoxymethoxy-1-(9-phenyl-9H-fluoren-9-yl)-1a,2,3,8,9,9a-hexahydro-1H-1,3-diaza-benzo[a]cyclopropa[e]cycloocten-8-ylmethyl ester