(S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol

Base Information

• Chemical Name: (S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol
• CAS No.: 1429033-46-4
• Molecular Formula: C₂₇H₃₈O₄Si
• Molecular Weight: 454.682
• Mol file: 1429033-46-4.mol

Synonyms:(S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol

Chemical Property of (S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol

There total 1 articles about (S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-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:

isopropenylmagnesium bromide (13291-18-4) + [(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde (171232-50-1) → (R)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol (1429033-45-3) + (S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol (1429033-46-4)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃; for 3h; Overall yield = 87 %; Overall yield = 1.18 g; Inert atmosphere;

DOI:10.1021/jo400029u

Reference yield: 94.0%

R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid (20445-31-2) + (S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol (1429033-46-4) → C37H45F3O6Si (1429033-68-0)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 96h; Inert atmosphere;

DOI:10.1021/jo400029u

Reference yield: 85.0%

(S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-ol (1429033-46-4) + methyl chloroformate (79-22-1) → (S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-yl methyl carbonate (1429033-47-5)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 20 ℃; for 22h; Inert atmosphere;

DOI:10.1021/jo400029u

upstream raw materials:

isopropenylmagnesium bromide

[(4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde

Downstream raw materials:

C₃₇H₄₅F₃O₆Si

C₃₇H₄₅F₃O₆Si

(S)-1-[(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbut-3-en-2-yl methyl carbonate