(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

Base Information

• Chemical Name: (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
• CAS No.: 488097-21-8
• Molecular Formula: C₄₁H₄₅N₃O₉
• Molecular Weight: 723.823
• Mol file: 488097-21-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 15 articles about (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 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: 92.0%

acetic anhydride (108-24-7) + 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 (488097-26-3) → (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 (488097-21-8)

Guidance literature:

With sodium acetate; at 20 ℃; for 1h;

DOI:10.1021/jo0206521

Reference yield:

9-bromo-9-phenyl-9H-fluorene (55135-66-5) → (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 (488097-21-8)

Guidance literature:

Multi-step reaction with 13 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

12.1: 63 percent / Davis' oxaziridine / tetrahydrofuran / 3 h / 20 °C

13.1: 92 percent / sodium acetate / 1 h / 20 °C

With pyridine; tert.-butylhydroperoxide; potassium phosphate; lithium aluminium tetrahydride; lead(II) nitrate; oxalyl dichloride; tetraethylammonium bromide; hydrogen; sodium acetate; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; spiro[(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3'-N-phenylsulfonyloxaziridine]; 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-5-hydroxy-7-methoxymethoxy-(3,4)-[N-(9-phenylfluoren-9-yl)aziridino]-3,4,5,6-tetrahydro-2H-benzo[b]azocin-1-yl acetate (488097-21-8)

Guidance literature:

Multi-step reaction with 13 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

12.1: 63 percent / Davis' oxaziridine / tetrahydrofuran / 3 h / 20 °C

13.1: 92 percent / sodium acetate / 1 h / 20 °C

With pyridine; tert.-butylhydroperoxide; potassium phosphate; lithium aluminium tetrahydride; lead(II) nitrate; oxalyl dichloride; tetraethylammonium bromide; hydrogen; sodium acetate; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; dimethyl sulfoxide; spiro[(1R,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3'-N-phenylsulfonyloxaziridine]; phenol; 10percent Pd/C; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 5.1: Swern oxidation;

DOI:10.1021/jo0206521

upstream raw materials:

acetic anhydride

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

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

Downstream raw materials:

(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