(3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one

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Chemical Name:(3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one
CAS No.:440351-22-4
Molecular Formula:C₂₆H₄₂O₆Si
Molecular Weight:478.701
Hs Code.:

Synonyms:(3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one

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Chemical Property of (3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one

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Technology Process of (3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one

There total 9 articles about (3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-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:

: 440351-20-2
(3aR,5R,6S,6aR)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

: 440351-22-4
(3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(02)00191-0

Reference yield:

: 57569-46-7
5-chloro-5-deoxy-1,2-O-isopropylidene-β-L-idofuranuronic acid-3,6-lactone

: 440351-22-4
(3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 90 percent / AIBN / benzene / Heating

2.1: 90 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: 70 percent / PTSA / CH₂Cl₂ / 3 h

4.1: 75 percent / BH₃*DMS; NaOAc; H₂O₂

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

5.2: 75 percent / diethyl ether; tetrahydrofuran / 2 h / 20 °C

6.1: 80 percent / NaH / dimethylformamide / 20 °C

7.1: 85 percent / H₂SO₄ / methanol

8.1: 90 percent / imidazole / CH₂Cl₂ / 20 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; sodium acetate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(02)00191-0

Reference yield:

: 440351-12-2
5-C-allyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranurono-6,3-lactone

: 440351-22-4
(3aR,5R,6aS)-5-[(S)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-pentyl]-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-6-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 90 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 - 20 °C

2.1: 70 percent / PTSA / CH₂Cl₂ / 3 h

3.1: 75 percent / BH₃*DMS; NaOAc; H₂O₂

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4.2: 75 percent / diethyl ether; tetrahydrofuran / 2 h / 20 °C

5.1: 80 percent / NaH / dimethylformamide / 20 °C

6.1: 85 percent / H₂SO₄ / methanol

7.1: 90 percent / imidazole / CH₂Cl₂ / 20 °C

8.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; oxalyl dichloride; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; sodium acetate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)00191-0