(3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one

Base Information

Chemical Name:(3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one
CAS No.:351340-29-9
Molecular Formula:C₂₆H₃₅NO₄
Molecular Weight:425.568
Hs Code.:

Synonyms:(3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one

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Chemical Property of (3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one

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Technology Process of (3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one

There total 11 articles about (3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one 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:

: 351340-41-5
(3R,4R)-1-Benzyl-3-benzyloxy-4-[(1S,2S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-nonyl]-azetidin-2-one

: 351340-29-9
(3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/jo001786m

Reference yield:

: 7367-85-3
methyl (E)-dec-2-enoate

: 351340-29-9
(3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: AD-Mix-α

2: Im / dimethylformamide

3: DIBAL-H / toluene; hexane / -78 °C

4: triphosgene; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 4A MS / CH₂Cl₂ / 1 h / 0 °C

6: 8.38 g / Et₃N / CH₂Cl₂ / 20 °C

7: TBAF / tetrahydrofuran / 2 h / 20 °C

With AD-mix-α; bis(trichloromethyl) carbonate; impramine; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo001786m

Reference yield:

: 351340-31-3
(2R,3S)-2,3-Dihydroxy-decanoic acid methyl ester

: 351340-29-9
(3R,4S)-1-Benzyl-3-benzyloxy-4-((1S,2S)-1,2-dihydroxy-nonyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: Im / dimethylformamide

2: DIBAL-H / toluene; hexane / -78 °C

3: triphosgene; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 4A MS / CH₂Cl₂ / 1 h / 0 °C

5: 8.38 g / Et₃N / CH₂Cl₂ / 20 °C

6: TBAF / tetrahydrofuran / 2 h / 20 °C

With bis(trichloromethyl) carbonate; impramine; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo001786m