2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester

Base Information

Chemical Name:2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester
CAS No.:78442-65-6
Molecular Formula:C₂₉H₃₇NO₆Si
Molecular Weight:523.701
Hs Code.:

2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester

Synonyms:2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester

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Chemical Property of 2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester

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Technology Process of 2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester

There total 7 articles about 2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester 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: 92.0%

: 3-Cyano-2-((3aR,4R,6S,6aS)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid methyl ester

: 58479-61-1
tert-butylchlorodiphenylsilane

: 78442-65-6
2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide;
DOI:10.1021/ja00403a052

Reference yield:

: 78442-62-3
(1S,2S,6S,7S,8R)-4,4-Dimethyl-9-oxo-3,5,10-trioxa-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid methyl ester

: 78442-65-6
2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / potassium tert-butoxide / tetrahydrofuran / Ambient temperature

2: aq. sodium bicarbonate / 0.5 h / Ambient temperature

3: 72 percent / BH₃*THF

4: 92 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide

With 1H-imidazole; dmap; borane-THF; potassium tert-butylate; sodium hydrogencarbonate; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ja00403a052

Reference yield:

: 142968-15-8
3-[1-Methoxycarbonyl-meth-(E)-ylidene]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester

: 78442-65-6
2-[(3aR,4R,6S,6aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: OsO₄, aq. H₂O₂ / 2-methyl-propan-2-ol / 22 h

2: 68 percent / CuSO₄, dl-10-camphorsulfonic acid / acetone

3: 70 percent / O₃, dimethylsulfide / CH₂Cl₂ / -78 °C

4: 95 percent / potassium tert-butoxide / tetrahydrofuran / Ambient temperature

5: aq. sodium bicarbonate / 0.5 h / Ambient temperature

6: 72 percent / BH₃*THF

7: 92 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide

With 1H-imidazole; dmap; osmium(VIII) oxide; borane-THF; dimethylsulfide; camphor-10-sulfonic acid; potassium tert-butylate; dihydrogen peroxide; sodium hydrogencarbonate; ozone; copper(II) sulfate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/ja00403a052