(1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde

Base Information

Chemical Name:(1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde
CAS No.:946392-54-7
Molecular Formula:C₂₆H₃₄O₄Si
Molecular Weight:438.639
Hs Code.:

Synonyms:(1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde

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Chemical Property of (1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde

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Technology Process of (1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde

There total 7 articles about (1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde 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: 85.0%

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

: 946392-54-7
(1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
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

: 946392-54-7
(1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2: 82 percent / sodium sulphate; copper sulphate; aq. HCl / 12 h

3: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With hydrogenchloride; lithium aluminium tetrahydride; copper(I) sulfate; Dess-Martin periodane; sodium sulfate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol0710616

Reference yield:

: 946392-50-3
(1R,4S,5R,6S)-6-hydroxy-4-pivaloyloxymethyl-3-oxabicyclo[3.2.0]heptan-2-one

: 946392-54-7
(1R,2S,3S)-3-tert-butyldiphenylsilyloxy-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]cyclobutane-1-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / imidazole / CH₂Cl₂ / 20 °C

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

3: 82 percent / sodium sulphate; copper sulphate; aq. HCl / 12 h

4: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; copper(I) sulfate; Dess-Martin periodane; sodium sulfate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol0710616