(3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol

Base Information

• Chemical Name: (3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol
• CAS No.: 737763-65-4
• Molecular Formula: C₄₆H₇₀O₃Si
• Molecular Weight: 699.145
• Mol file: 737763-65-4.mol

Synonyms:(3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol

Chemical Property of (3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol

There total 11 articles about (3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-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: 56.0%

(all-E)-5-<(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-enyl>-3-methyl-2,4-pentadienyltriphenylphosphonium bromide + (2E,4E,6E,8E,10E,12E)-2,7,11-trimethyl-13-[(1R,4S,6R)-2,2,6-trimethyl-6-triethylsilyloxy-7-oxabicyclo[2.2.1]hept-1-yl]trideca-2,4,6,8,10,12-hexaenal (737763-64-3) → (3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol (737763-65-4)

Guidance literature:

With sodium methylate;

DOI:10.1248/cpb.52.780

Reference yield:

(-)-(1S,4S,6R)-4-(tert-butyldimethylsilyloxy)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde (439859-70-8) → (3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol (737763-65-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / NaH

2: 96 percent / HF; pyridine

3: 54 percent / (BrC₆H₄)3NSbCl₆ / CH₂Cl₂ / 2 h / 20 °C

4: lutidine

5: DIBAL-H

6: NaOMe

7: Dowex 50W-X₈ (H+)

8: 56 percent / NaOMe

With pyridine; (BrC₆H₄)3NSbCl₆; Dowex 50W-X₈ (H+); lutidine; hydrogen fluoride; sodium methylate; sodium hydride; diisobutylaluminium hydride; In dichloromethane; 1: Emmons-Horner reaction / 6: Wittig condensation / 8: Wittig condensation;

DOI:10.1248/cpb.52.780

Reference yield:

(2E,4E)-5-[(1S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-3-methyl-penta-2,4-dienoic acid ethyl ester (395089-70-0) → (3R,3'S,5'R,6'R)-3',6'-epoxy-5,6-dihydro-5'-triethylsilyloxy-β,β-caroten-3-ol (737763-65-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / HF; pyridine

2: 45 percent / (BrC₆H₄)3NSbCl₆ / CH₂Cl₂ / 0.33 h / 20 °C

3: lutidine

4: LiAlH₄

5: MnO₂

6: NaOMe

7: Dowex 50W-X₈ (H+)

8: 56 percent / NaOMe

With pyridine; manganese(IV) oxide; lithium aluminium tetrahydride; (BrC₆H₄)3NSbCl₆; Dowex 50W-X₈ (H+); lutidine; hydrogen fluoride; sodium methylate; In dichloromethane; 6: Wittig condensation / 8: Wittig condensation;

DOI:10.1248/cpb.52.780

upstream raw materials:

(2E,4E,6E,8E,10E,12E)-2,7,11-trimethyl-13-[(1R,4S,6R)-2,2,6-trimethyl-6-triethylsilyloxy-7-oxabicyclo[2.2.1]hept-1-yl]trideca-2,4,6,8,10,12-hexaenal

(2E,4E)-5-[(1S,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl]-3-methyl-penta-2,4-dienoic acid ethyl ester

(-)-(1S,4S,6R)-4-(tert-butyldimethylsilyloxy)-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptane-1-carbaldehyde

(2E,4E)-5-[(1R,2R,4S)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]hept-1-yl]-3-methylpenta-2,4-dienenitrile

Downstream raw materials:

(all-E,3S,3'R,5R,6R)-3,6-epoxy-5,6-dihydro-β,β-carotene-3',5-diol