(3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol

Base Information

• Chemical Name: (3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol
• CAS No.: 105545-03-7
• Molecular Formula: C₆₃H₈₀O₈
• Molecular Weight: 965.323

Synonyms:(3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol

Chemical Property of (3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol

There total 2 articles about (3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol 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: 22.8%

(2S,3R,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5,6,9,11,12,13-Heptahydroxy-2,4,6,8,10,12-hexamethyl-1-pentadecanol (105545-05-9) + benzyl chloride (100-44-7) → (3R,4S,5R,6R,7S,8R,10R,11R,12S,13R,14S)-3,7,11,13,15-Pentakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,5,10-triol (105545-06-0) + (3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol (105545-03-7)

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide; at 22 ℃; for 6.5h; Further byproducts given;

DOI:10.1016/S0040-4039(00)84383-X

Reference yield:

(3S,4R,6R,7R,8S,9R,10S)-7,9,11-Tris-benzyloxy-2-[(4R,5R)-5-((R)-1-benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-6-(tert-butyl-dimethyl-silanyloxy)-4,6,8,10-tetramethyl-undecan-3-ol (105565-34-2,124990-93-8) + benzyl chloride (100-44-7) → (3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol (105545-03-7)

Guidance literature:

With potassium hydroxide; hydrogen fluoride; Yield given. Multistep reaction; 1.) MeCN 24 deg C, 1 h, 2.) DMF, 24 deg C, 5h;

DOI:10.1016/S0040-4039(00)84383-X

Reference yield: 93.0%

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + (3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-3,5,7,11,13,15-Hexakis-benzyloxy-4,6,8,10,12,14-hexamethyl-pentadecane-4,10-diol (105545-03-7) → 1,3,5,9,11,13-hexa-O-benzyl-2,4,7,8,10,14,15-heptadeoxy-2,4,6,8,10,12-hexa-C-methyl-6,12-di-O-triethylsilyl-D-arabino-D-gluco-L-ido-pentadecitol (105545-07-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 23 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)84383-X

upstream raw materials:

(2S,3R,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3,5,6,9,11,12,13-Heptahydroxy-2,4,6,8,10,12-hexamethyl-1-pentadecanol

benzyl chloride

(3S,4R,6R,7R,8S,9R,10S)-7,9,11-Tris-benzyloxy-2-[(4R,5R)-5-((R)-1-benzyloxy-propyl)-2,2,5-trimethyl-[1,3]dioxolan-4-yl]-6-(tert-butyl-dimethyl-silanyloxy)-4,6,8,10-tetramethyl-undecan-3-ol

Downstream raw materials:

1,3,5,9,11,13-hexa-O-benzyl-2,4,7,8,10,14,15-heptadeoxy-2,4,6,8,10,12-hexa-C-methyl-6,12-di-O-triethylsilyl-D-arabino-D-gluco-L-ido-pentadecitol

(3R,4R,5R,6S,7S,8R,10R,11R,12S,13R,14S)-15-(tert-Butyl-diphenyl-silanyloxy)-4,6,8,10,12,14-hexamethyl-4,10-bis-triethylsilanyloxy-pentadecane-3,5,7,11,13-pentaol

1-O-t-butyldiphenylsilyl-2,4,7,8,10,14,15-heptadeoxy-3,5:9,11-di-O-isopropylidene-2,4,6,8,10,12-hexa-C-methyl-6,12-di-O-triethylsilyl-D-arabino-D-gluco-L-ido-pentadecitol

(2S,3S,4R,6R)-6-{(4R,5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-2-((4R,5R,6R)-6-ethyl-2,2,5-trimethyl-5-triethylsilanyloxy-[1,3]dioxan-4-yl)-4-methyl-6-triethylsilanyloxy-heptan-3-ol

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