(1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol

Base Information

• Chemical Name: (1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol
• CAS No.: 681433-46-5
• Molecular Formula: C₃₁H₃₈O₄Si
• Molecular Weight: 502.726
• Mol file: 681433-46-5.mol

Synonyms:(1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol

Chemical Property of (1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol

There total 5 articles about (1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol 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: 78.0%

(R)-[tert-butyl(diphenylsilyl)oxy](phenyl)acetaldehyde (172034-27-4) + (2S)-ethoxy-(4S)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran (596093-06-0) → (1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol (681433-46-5)

Guidance literature:

In toluene; at 70 ℃; for 48h;

DOI:10.1055/s-2005-868518

Reference yield:

(tert-butyl-diphenyl-silanyloxy)-phenyl-acetaldehyde (306961-33-1) + (2S)-ethoxy-(4S)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran (596093-06-0) → (1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol (681433-46-5) + (1R,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((2S,6R)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl)-2-phenyl-ethanol

Guidance literature:

(tert-butyl-diphenyl-silanyloxy)-phenyl-acetaldehyde; (2S)-ethoxy-(4S)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran; In toluene; at 70 ℃; for 12h;

With ammonium chloride; In toluene; Further stages. Title compound not separated from byproducts.;

DOI:10.1002/adsc.200303127

Reference yield:

(tert-butyl-diphenyl-silanyloxy)-phenyl-acetic acid methyl ester (859520-64-2) → (1S,2R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[(2R,6S)-6-ethoxy-5,6-dihydro-2H-pyran-2-yl]-2-phenylethanol (681433-46-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / i-Bu₂AlH / diethyl ether / 0.5 h / -78 °C

2: 78 percent / toluene / 48 h / 70 °C

With diisobutylaluminium hydride; In diethyl ether; toluene;

DOI:10.1055/s-2005-868518

upstream raw materials:

(tert-butyl-diphenyl-silanyloxy)-phenyl-acetaldehyde

(2S)-ethoxy-(4S)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-pyran

(R)-[tert-butyl(diphenylsilyl)oxy](phenyl)acetaldehyde

(tert-butyl-diphenyl-silanyloxy)-phenyl-acetic acid methyl ester

Downstream raw materials:

C₂₉H₃₂O₃Si

C₂₉H₃₂O₄Si

(R)-6-((1R,2R)-1-Benzyloxy-2-hydroxy-2-phenyl-ethyl)-5,6-dihydro-pyran-2-one

(+)-goniodiol