(2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde

Base Information

Chemical Name:(2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde
CAS No.:913174-74-0
Molecular Formula:C₂₃H₂₆O₅Si
Molecular Weight:410.542
Hs Code.:

Synonyms:(2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde

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Chemical Property of (2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde

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Technology Process of (2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde

There total 3 articles about (2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-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:

: 913174-86-4
(3aR,5R,6S,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

: 58479-61-1
tert-butylchlorodiphenylsilane

: 913174-74-0
(2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde

Guidance literature:: (3aR,5R,6S,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one; tert-butylchlorodiphenylsilane; With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 72h;

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃; for 3h;

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 ℃; for 0.583333h;
DOI:10.3987/COM-06-10786

Reference yield:

: 2033-24-1
cycl-isopropylidene malonate

: 913174-74-0
(2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1.1: 61 percent / t-BuNH₂ / dimethylformamide / 120 h / 40 °C

2.1: 90 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / 20 °C

3.1: imidazole; DMAP / CH₂Cl₂ / 72 h / 20 °C

3.2: HF*Py / tetrahydrofuran / 3 h / 0 °C

3.3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.58 h / -60 °C

With 1H-imidazole; dmap; tert-butylamine; In dichloromethane; N,N-dimethyl-formamide; 3.3: Swern oxidation;
DOI:10.3987/COM-06-10786

Reference yield:

: 35784-82-8
(4R,6R,7S,8S)-7-hydroxy-6-hydroxymethyl-1,5-dioxa-2-oxobicyclo[3.3.0^4,8]octane

: 913174-74-0
(2S,3R,3aS,6aR)-3-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-hexahydro-furo[3,2-b]furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1.1: 90 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: imidazole; DMAP / CH₂Cl₂ / 72 h / 20 °C

2.2: HF*Py / tetrahydrofuran / 3 h / 0 °C

2.3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.58 h / -60 °C

With 1H-imidazole; dmap; In dichloromethane; 2.3: Swern oxidation;
DOI:10.3987/COM-06-10786