(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

Base Information

• Chemical Name: (2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one
• CAS No.: 868134-45-6
• Molecular Formula: C₃₁H₄₄O₅Si
• Molecular Weight: 524.773
• Mol file: 868134-45-6.mol

Synonyms:(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

Chemical Property of (2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

There total 1 articles about (2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one 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: 88.0%

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) + (2S)-1,2-O-cyclohexylidene-1,2-dihydroxypentan-3-one (308795-19-9) → (2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one (868134-45-6)

Guidance literature:

(2S)-1,2-O-cyclohexylidene-1,2-dihydroxypentan-3-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at 0 ℃; for 0.5h;

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal; In diethyl ether; at 0 ℃; for 5h;

DOI:10.1021/jo051307p

Reference yield:

(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one (868134-45-6) → (1S,2R,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-1-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2,4-dimethyl-pentane-1,3-diol

Guidance literature:

With lithium borohydride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h;

DOI:10.1021/jo051307p

Reference yield:

(2R,3S,4R)-5-(tert-butyldiphenylsilyloxy)-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one (868134-45-6) → tert-Butyl-[(R)-2-((4S,5R,6S)-6-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propoxy]-diphenyl-silane

Guidance literature:

Multi-step reaction with 2 steps

1: LiBH₄ / diethyl ether; tetrahydrofuran / 2 h / -78 °C

2: p-toluenesulfonic acid / acetone / 20 °C

With lithium borohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; acetone;

DOI:10.1021/jo051307p

upstream raw materials:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

(2S)-1,2-O-cyclohexylidene-1,2-dihydroxypentan-3-one