(2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone

Base Information

• Chemical Name: (2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone
• CAS No.: 911218-17-2
• Molecular Formula: C₂₅H₃₇N₂O₃P
• Molecular Weight: 444.554

Synonyms:(2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone

Chemical Property of (2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone

Chemical Property:

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Technology Process of (2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone

There total 4 articles about (2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ⁵-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone 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: 72.0%

2-benzyloxymethyl-cyclopent-2-enone (911218-16-1) + (3aR,7aR)-2-crotyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide (150932-41-5) → (2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone (911218-17-2)

Guidance literature:

(3aR,7aR)-2-crotyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

2-benzyloxymethyl-cyclopent-2-enone; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

DOI:10.1021/ol0615230

Reference yield:

cyclopent-2-enone (930-30-3) → (2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone (911218-17-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 84 percent / Br₂; Et₃N / CH₂Cl₂ / 0 - 20 °C

2.1: 67 percent / p-toluenesulfonic acid / benzene / 18 h / Heating

3.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

3.2: 94 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1 h / -78 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

4.2: 72 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

With n-butyllithium; bromine; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; benzene;

DOI:10.1021/ol0615230

Reference yield:

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene (68241-78-1) → (2R,3S)-2-Benzyloxymethyl-3-[(E)-(R)-3-((3aR,7aR)-1,3-dimethyl-2-oxo-octahydro-2λ5-benzo[1,3,2]diazaphosphol-2-yl)-1-methyl-allyl]-cyclopentanone (911218-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 94 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C

2.2: 72 percent / tetrahydrofuran; hexane / 0.75 h / -78 °C

With n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1021/ol0615230

upstream raw materials:

2-benzyloxymethyl-cyclopent-2-enone

(3aR,7aR)-2-crotyloctahydro-1H-1,3-dimethyl-1,3,2-benzadiazaphosphole 2-oxide

cyclopent-2-enone

6-bromo-1,4-dioxa-spiro[4.4]non-6-ene

Downstream raw materials:

2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-hydroxycyclopentanone

2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-cyclopentanol

2-benzyloxymethyl-3-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-cyclopentanone

5-benzyloxymethyl-4-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-cyclopent-2-enone

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