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

Base Information

• Chemical Name: (1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol
• CAS No.: 952418-10-9
• Molecular Formula: C₂₇H₃₆O₄Si
• Molecular Weight: 452.666
• Mol file: 952418-10-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-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: 96.0%

vinyl magnesium bromide (1826-67-1) + (-)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-one (681853-95-2) → (1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol (952418-10-9)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/j.tet.2007.06.100

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol (952418-10-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / triethylamine; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

2.2: 86 percent / tetrahydrofuran / 7 h / 0 - 20 °C

3.1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4.1: 96 percent / tetrahydrofuran / 1 h / -78 °C

With dmap; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2.2: Wittig reaction / 3.1: Swern oxidation / 4.1: Grignard reaction;

DOI:10.1016/j.tet.2007.06.100

Reference yield:

(1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(tert-butyldiphenylsilyloxy)ethan-1-ol (681853-93-0) → (1R)-(+)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-1-[(tert-butyldiphenylsilyloxy)methyl]-2-propen-1-ol (952418-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 96 percent / tetrahydrofuran / 1 h / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Swern oxidation / 2: Grignard reaction;

DOI:10.1016/j.tet.2007.06.100

upstream raw materials:

vinyl magnesium bromide

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

D-ribose

tert-butylchlorodiphenylsilane

Downstream raw materials:

(1R,4R,5S)-9-[3-(tert-butyldiphenylsilyloxymethyl)-4,5-isopropylidenedioxy-2-cyclopenten-1-yl]-N⁶,N⁶-bis(tert-butoxycarbonyl)adenine

(1R,4R,5S)-9-[3-(tert-butyldiphenylsilyloxymethyl)-4,5-isopropylidenedioxy-2-cyclopenten-1-yl]adenine

neplanocin A

(3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol