(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

Base Information

• Chemical Name: (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
• CAS No.: 440351-20-2
• Molecular Formula: C₂₆H₄₄O₆Si
• Molecular Weight: 480.717

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (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

There total 8 articles about (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 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: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3aR,5R,6S,6aR)-5-((S)-4-Benzyloxy-1-hydroxymethyl-pentyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (440351-19-9) → (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 (440351-20-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(02)00191-0

Reference yield:

5-chloro-5-deoxy-1,2-O-isopropylidene-β-L-idofuranuronic acid-3,6-lactone (57569-46-7) → (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 (440351-20-2)

Guidance literature:

Multi-step reaction with 8 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

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:

5-C-allyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranurono-6,3-lactone (440351-12-2) → (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 (440351-20-2)

Guidance literature:

Multi-step reaction with 7 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

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

upstream raw materials:

tert-butyldimethylsilyl chloride

(3aR,5R,6S,6aR)-5-((S)-4-Benzyloxy-1-hydroxymethyl-pentyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

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

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

Downstream raw materials:

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

[(S)-5-Benzyloxy-2-((3aR,5R,6aR)-2,2-dimethyl-6-methylene-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexyloxy]-tert-butyl-dimethyl-silane

[(S)-5-Benzyloxy-2-((3aR,5S,6aR)-2,2-dimethyl-6-methylene-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexyloxy]-tert-butyl-dimethyl-silane

(3aR,5S,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

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