[(S)-2-(4-Benzyloxy-phenyl)-1-((1S,3aR,6aS)-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(S)-2-(4-Benzyloxy-phenyl)-1-((1S,3aR,6aS)-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 142596-96-1
• Molecular Formula: C₂₇H₃₃NO₅
• Molecular Weight: 451.563
• Mol file: 142596-96-1.mol

Synonyms:

Chemical Property of [(S)-2-(4-Benzyloxy-phenyl)-1-((1S,3aR,6aS)-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-2-(4-Benzyloxy-phenyl)-1-((1S,3aR,6aS)-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl ester

There total 20 articles about [(S)-2-(4-Benzyloxy-phenyl)-1-((1S,3aR,6aS)-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl 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:

1-[(S)-2-(4-Benzyloxy-phenyl)-1-tert-butoxycarbonylamino-ethyl]-3-oxo-tetrahydro-cyclopenta[c]furan-3a-carboxylic acid → [(S)-2-(4-Benzyloxy-phenyl)-1-(3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl ester (142596-96-1,142696-06-8)

Guidance literature:

In xylene; at 160 ℃; for 10h; Yield given;

DOI:10.1016/S0040-4039(00)79571-2

Reference yield:

(1S,3aR,6aS)-1-[(S)-2-(4-Benzyloxy-phenyl)-1-tert-butoxycarbonylamino-ethyl]-3-oxo-tetrahydro-cyclopenta[c]furan-3a-carboxylic acid → [(S)-2-(4-Benzyloxy-phenyl)-1-((1S,3aR,6aS)-3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl ester (142596-96-1)

Guidance literature:

In xylene; at 160 ℃; for 10h; Yield given;

DOI:10.1016/S0040-4039(00)79571-2

Reference yield:

O-benzyl-N-(tert-butoxycarbonyl)-L-tyrosinal (82689-15-4) → [(S)-2-(4-Benzyloxy-phenyl)-1-(3-oxo-hexahydro-cyclopenta[c]furan-1-yl)-ethyl]-carbamic acid tert-butyl ester (142596-96-1,142696-06-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / KNTMS₂ / tetrahydrofuran / 18 h / 0 - 25 °C

2: 1.) EtOCOCl, Et₃N, 2.)NaBH₄ / 1.) THF, -10 - -2 deg C, 45 min, 2.) MeOH, 0 deg C, 1 h

3: Et₃N / 0 °C

4: NaI / acetone / 3 h / 56 °C

5: NaH / dimethylformamide / 45 h / 80 °C

6: mCPBA / CH₂Cl₂ / 4 h / -10 - 25 °C

7: 98 percent / LiNTMS₂, ZnCl₂ / tetrahydrofuran; diethyl ether / 72 h / -20 - 25 °C

8: LiOH / dioxane; H₂O / 6 h / 25 °C

9: xylene / 10 h / 160 °C

With lithium hydroxide; sodium tetrahydroborate; chloroformic acid ethyl ester; potassium hexamethylsilazane; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; xylene;

DOI:10.1016/S0040-4039(00)79571-2

upstream raw materials:

O-benzyl-N-(tert-butoxycarbonyl)-L-tyrosinal

[(Z)-(S)-1-(4-Benzyloxy-benzyl)-6-hydroxy-hex-2-enyl]-carbamic acid tert-butyl ester

[(Z)-(S)-1-(4-Benzyloxy-benzyl)-6-iodo-hex-2-enyl]-carbamic acid tert-butyl ester

(Z)-(S)-7-(4-Benzyloxy-phenyl)-6-tert-butoxycarbonylamino-hept-4-enoic acid

Downstream raw materials:

[(1S,2S)-2-((1S,2R)-2-Benzylcarbamoyl-cyclopentyl)-2-hydroxy-1-(4-hydroxy-benzyl)-ethyl]-carbamic acid tert-butyl ester

(4S,5R)-4-(4-Benzyloxy-benzyl)-5-((1S,2R)-2-hydroxymethyl-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5S)-4-(4-Benzyloxy-benzyl)-5-((1R,2S)-2-hydroxymethyl-cyclopentyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

[(S)-2-(4-Benzyloxy-phenyl)-1-(3,3-dimethyl-hexahydro-cyclopenta[e][1,3]dioxepin-1-yl)-ethyl]-carbamic acid tert-butyl ester