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

Base Information

• Chemical Name: (3aR,3bS,8S,8aR,9aR)-8-(3-Benzyloxy-butyl)-2,2,5,5-tetramethyl-hexahydro-1,3,4,6,9-pentaoxa-cyclopenta[a]azulene
• CAS No.: 440351-18-8
• Molecular Formula: C₂₃H₃₄O₆
• Molecular Weight: 406.519
• Mol file: 440351-18-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (3aR,3bS,8S,8aR,9aR)-8-(3-Benzyloxy-butyl)-2,2,5,5-tetramethyl-hexahydro-1,3,4,6,9-pentaoxa-cyclopenta[a]azulene 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: 80.0%

benzyl bromide (100-39-0) + 4-((3aR,3bS,8S,8aR,9aR)-2,2,5,5-Tetramethyl-hexahydro-1,3,4,6,9-pentaoxa-cyclopenta[a]azulen-8-yl)-butan-2-ol (440351-17-7) → (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)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 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,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)

Guidance literature:

Multi-step reaction with 6 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

With lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; dihydrogen peroxide; sodium acetate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 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,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)

Guidance literature:

Multi-step reaction with 5 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

With lithium aluminium tetrahydride; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; sodium acetate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

benzyl bromide

4-((3aR,3bS,8S,8aR,9aR)-2,2,5,5-Tetramethyl-hexahydro-1,3,4,6,9-pentaoxa-cyclopenta[a]azulen-8-yl)-butan-2-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,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