(3aR,5R,6S,6aR)-5-((S)-4-Benzyloxy-1-hydroxymethyl-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-hydroxymethyl-pentyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
• CAS No.: 440351-19-9
• Molecular Formula: C₂₀H₃₀O₆
• Molecular Weight: 366.455

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (3aR,5R,6S,6aR)-5-((S)-4-Benzyloxy-1-hydroxymethyl-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: 85.0%

(3aR,3bS,8S,8aR,9aR)-8-(3-Benzyloxy-butyl)-2,2,5,5-tetramethyl-hexahydro-1,3,4,6,9-pentaoxa-cyclopenta[a]azulene (440351-18-8) → (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)

Guidance literature:

With sulfuric acid; In methanol;

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-hydroxymethyl-pentyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (440351-19-9)

Guidance literature:

Multi-step reaction with 7 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

With 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-hydroxymethyl-pentyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol (440351-19-9)

Guidance literature:

Multi-step reaction with 6 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

With 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:

(3aR,3bS,8S,8aR,9aR)-8-(3-Benzyloxy-butyl)-2,2,5,5-tetramethyl-hexahydro-1,3,4,6,9-pentaoxa-cyclopenta[a]azulene

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

5-C-allyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose

Downstream raw materials:

(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

[5-benzyloxy-2-(2,2-dimethyl-3a,6a-dihydro-furo[2,3-d][1,3]dioxol-5-yl)-hexyloxy]-tert-butyl-dimethyl-silane

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

(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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