2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol

Base Information

• Chemical Name: 2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol
• CAS No.: 1256338-97-2
• Molecular Formula: C₂₀H₃₄O₄Si
• Molecular Weight: 366.573
• Mol file: 1256338-97-2.mol

Synonyms:2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol

Chemical Property of 2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol

There total 10 articles about 2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol 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: 89.0%

(tert-butyl)[(R)-[ (4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methoxy]dimethylsilane → 2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol (1256338-97-2)

Guidance literature:

With borane-dimethyl sulfide complex; In tetrahydrofuran; at -78 ℃; for 0.333333h;

DOI:10.1002/hlca.201200656

Reference yield: 80.0%

(1R,2S,3R)-5-(benzyloxy)-1-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylpentane (1256338-96-1) → 2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol (1256338-97-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃;

DOI:10.1055/s-0030-1257858

Reference yield:

(R)-methyl mandelate (20698-91-3) → 2-{(4R,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol (1256338-97-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1H-imidazole / dichloromethane / 4 h / 0 °C

2: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -78 °C

3: toluene / 6 h / Reflux

4: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; water; tert-butyl alcohol / 14 h / 20 °C

5: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 0 - 20 °C

6: diisobutylaluminium hydride / dichloromethane; hexane / 0.33 h / -78 °C

7: potassium tert-butylate / tetrahydrofuran / 0.25 h / 0 - 20 °C

8: borane-dimethyl sulfide complex / tetrahydrofuran / 0.33 h / -78 °C

With 1H-imidazole; osmium(VIII) oxide; borane-dimethyl sulfide complex; potassium tert-butylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol; 3: |Wittig Olefination / 7: |Wittig Olefination;

DOI:10.1002/hlca.201200656

upstream raw materials:

(1R,2S,3R)-5-(benzyloxy)-1-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylpentane

(R)-methyl mandelate

tert-butyldimethylsilyl chloride

(R)-2-(t-butyldimethylsilyloxy)-2-phenylacetaldehyde

Downstream raw materials:

(4S,6R)-6-[(1R,2R)-1,2-dihydroxy-2-phenylethyl]-4-hydroxy-tetrahydro-2H-2-pyranone