(1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol

Base Information

• Chemical Name: (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol
• CAS No.: 681853-93-0
• Molecular Formula: C₂₅H₃₄O₄Si
• Molecular Weight: 426.628
• Mol file: 681853-93-0.mol

Synonyms:(1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol

Chemical Property of (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol

There total 10 articles about (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-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: 93.0%

Methyltriphenylphosphonium bromide (1779-49-3) + 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (96690-02-7) → (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol (681853-93-0)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose; In tetrahydrofuran; at 0 - 20 ℃; for 7h;

DOI:10.1021/jo0356762

Reference yield: 89.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (3aR,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (138127-67-0) → (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol (681853-93-0)

Guidance literature:

Methyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

(3aR,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol; In tetrahydrofuran; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1039/c5ob01042j

Reference yield: 86.0%

methylphosphonium bromide + 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (96690-02-7) → (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol (681853-93-0)

Guidance literature:

methylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose; In tetrahydrofuran; at 0 - 20 ℃; for 7h;

DOI:10.1002/chem.200802629

upstream raw materials:

Methyltriphenylphosphonium bromide

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

2,3-O-isopropylidene-D-ribofuranose

D-ribose

Downstream raw materials:

(3aR,4R,6aR)-(6-benzyloxymethyl-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yloxy)-tert-butyl-diphenyl-silane

RX-3117

(3R,4S,5S)-3-(benzyloxymethyl)-1,6-dien-4,5-(O-isopropylidenedioxy)-heptan-3-ol

Refernces

• 1、 -. "COMPOUNDS AND METHODS FOR TREATING ADDICTION AND RELATED DISORDERS". Paragraph 00168. . Retrieved 2019/08/29.
• 2、 Srihari,Sathish Reddy,Yadav,Yedlapudi,Kalivendi, Shasi V.. "First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B". . p. 5616 - 5618. Retrieved 2013/09/23.