3,3'-O-[1,18-octadecan-(cis-8,11-methylidene)methylene]-2,2'-di-O-[3-(R)-7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol

Base Information

• Chemical Name: 3,3'-O-[1,18-octadecan-(cis-8,11-methylidene)methylene]-2,2'-di-O-[3-(R)-7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol
• CAS No.: 427893-81-0
• Molecular Formula: C₅₂H₉₆O₆
• Molecular Weight: 817.331
• Mol file: 427893-81-0.mol

Synonyms:3,3'-O-[1,18-octadecan-(cis-8,11-methylidene)methylene]-2,2'-di-O-[3-(R)-7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol

Chemical Property of 3,3'-O-[1,18-octadecan-(cis-8,11-methylidene)methylene]-2,2'-di-O-[3-(R)-7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,3'-O-[1,18-octadecan-(cis-8,11-methylidene)methylene]-2,2'-di-O-[3-(R)-7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol

There total 9 articles about 3,3'-O-[1,18-octadecan-(cis-8,11-methylidene)methylene]-2,2'-di-O-[3-(R)-7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol 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: 59.0%

benzyl bromide (100-39-0) + (R)-2-((R)-3,7-Dimethyl-octyloxy)-3-[7-(3-{7-[(R)-2-((R)-3,7-dimethyl-octyloxy)-3-hydroxy-propoxy]-heptyl}-cyclopentyl)-heptyloxy]-propan-1-ol (222984-27-2) → 3,3'-O-[1,18-octadecan-(cis-8,11-methylidene)methylene]-2,2'-di-O-[3-(R)-7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol (427893-81-0)

Guidance literature:

(R)-2-((R)-3,7-Dimethyl-octyloxy)-3-[7-(3-{7-[(R)-2-((R)-3,7-dimethyl-octyloxy)-3-hydroxy-propoxy]-heptyl}-cyclopentyl)-heptyloxy]-propan-1-ol; With 15-crown-5; sodium hydride; In tetrahydrofuran; for 0.166667h;

benzyl bromide; In tetrahydrofuran; Heating;

DOI:10.1021/ja049805n

Reference yield: 50.0%

benzyl bromide (100-39-0) + 3,3'-O-<1,18-octadecan-(8,11-methylidene)methylene>-bis<2-O-<(R)-3,7-dimethyloctyl>-sn-glycerol> (222984-27-2) → C59H102O6 (222984-22-7) + 3,3'-O-[1,18-octadecan-(8,11-methylidene)methylene]-2,2'-di-O-[(R)-3,7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol (427893-81-0)

Guidance literature:

With silver(l) oxide; In dichloromethane; for 7h; Heating;

DOI:10.1002/1521-3765(20020201)8:3<585::AID-CHEM585>3.0.CO;2-5

Reference yield:

cis-cyclopentane-1,3-dicarboxaldehyde (10283-91-7) → 3,3'-O-[1,18-octadecan-(cis-8,11-methylidene)methylene]-2,2'-di-O-[3-(R)-7-dimethyloctyl]-1'-O-benzyl-sn-diglycerol (427893-81-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 56 percent / NaBH₄ / methanol / 20 °C

2.1: I₂; imidazole / diethyl ether; acetonitrile / 72 h / 20 °C

2.2: 50 percent / acetonitrile / 48 h / Heating

3.1: n-BuLi / tetrahydrofuran / 20 h / 0 °C

3.2: 55 percent / tetrahydrofuran

4.1: 97 percent / H₂ / Pd/C / ethanol / 24 h / 20 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

6.1: KH / tetrahydrofuran

6.2: 125 mg / tetrahydrofuran / 20 °C

7.1: 89 percent / H₂ / Pd/C / ethyl acetate / 20 °C

8.1: 15-crown-5; NaH / tetrahydrofuran / 0.17 h

8.2: 59 percent / tetrahydrofuran / Heating

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; 15-crown-5; hydrogen; iodine; potassium hydride; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/ja049805n

upstream raw materials:

benzyl bromide

3,3'-O-<1,18-octadecan-(8,11-methylidene)methylene>-bis<2-O-<(R)-3,7-dimethyloctyl>-sn-glycerol>

(R)-2-((R)-3,7-Dimethyl-octyloxy)-3-[7-(3-{7-[(R)-2-((R)-3,7-dimethyl-octyloxy)-3-hydroxy-propoxy]-heptyl}-cyclopentyl)-heptyloxy]-propan-1-ol

cis-cyclopentane-1,3-dicarboxaldehyde

Downstream raw materials:

3,3'-O-[1,18-octadecan-(8,11-methylidene)methylene]-2,2'-di-O-[(R)-3,7-dimethyloctyl]-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1'-O-benzyl-sn-diglycerol

3,3'-O-[1,18-octadecan-(8,11-methylidene)methylene]-2,2'-di-O-[(R)-3,7-dimethyloctyl]-1-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-1'-O-(dibenzylphosphono)-sn-diglycerol