{(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate

Base Information

Chemical Name:{(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate
CAS No.:946392-57-0
Molecular Formula:C₁₈H₂₄O₇S
Molecular Weight:384.45
Hs Code.:

Synonyms:{(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate

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Chemical Property of {(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate

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Technology Process of {(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate

There total 10 articles about {(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate 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: 93.0%

: 946392-44-5
{(1S,2R,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxycyclobutyl}methyl benzoate

: 124-63-0
methanesulfonyl chloride

: 946392-57-0
{(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ol0710616

Reference yield:

: 946392-51-4
(1R,4S,5S,6S)-6-tert-butyldiphenylsilyloxy-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one

: 946392-57-0
{(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 88 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2.1: 82 percent / sodium sulphate; copper sulphate; aq. HCl / 12 h

3.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: sodium carbonate / methanol / 4 h

4.2: 88 percent / NaBH₄ / methanol / 0.33 h

5.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

6.1: 97 percent / TBAF / tetrahydrofuran / 2 h

7.1: 93 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; copper(I) sulfate; tetrabutyl ammonium fluoride; sodium carbonate; Dess-Martin periodane; sodium sulfate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol0710616

Reference yield:

: 946392-43-4
{(1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutyl}methanol

: 946392-57-0
{(1S,2S,3S)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(methylsulfonyloxy)cyclobutyl}methyl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2.1: sodium carbonate / methanol / 4 h

2.2: 88 percent / NaBH₄ / methanol / 0.33 h

3.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

4.1: 97 percent / TBAF / tetrahydrofuran / 2 h

5.1: 93 percent / Et₃N / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; sodium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol0710616