(3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS No.: 855855-54-8
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 855855-54-8.mol

Synonyms:(3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property of (3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole

There total 8 articles about (3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole 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: 98.0%

(3aR,5S,6aR)-2,2-Dimethyl-5-((E)-styryl)-tetrahydro-furo[2,3-d][1,3]dioxole (855855-55-9) → (3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole (855855-54-8)

Guidance literature:

With hydrogen; nickel; In ethanol; under 3102.89 Torr;

DOI:10.1016/j.tetlet.2005.04.031

Reference yield: 91.0%

C15H18O4 → (3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole (855855-54-8)

Guidance literature:

With 10 wt% Pd(OH)2 on carbon; hydrogen; In ethanol;

DOI:10.1002/ejoc.201801211

Reference yield:

O1,O2-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose (4613-68-7,14260-67-4,22248-90-4,74996-06-8) → (3aR,5R,6aR)-2,2-Dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxole (855855-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / n-BuLi / tetrahydrofuran / 0 - 20 °C

2: 98 percent / H₂ / Raney-Ni / ethanol / 3102.89 Torr

With n-butyllithium; hydrogen; nickel; In tetrahydrofuran; ethanol; 1: Wittig olefination;

DOI:10.1016/j.tetlet.2005.04.031

upstream raw materials:

(3aR,5S,6aR)-2,2-Dimethyl-5-((E)-styryl)-tetrahydro-furo[2,3-d][1,3]dioxole

O¹,O²-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose

3-deoxy-1,2-O-isopropylidene-D-glucose

3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

Downstream raw materials:

(3R,5R)-trans-3,5-dihydroxy-1,7-diphenyl-1-heptene

Benzoic acid (1S,3S,7R)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-9-(4-methoxy-benzyloxy)-1-phenethyl-non-5-ynyl ester

(E)-(3S,5S,9R)-9-(tert-Butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-1-phenyl-undec-7-ene-3,5-diol

tert-Butyl-{(E)-(R)-4-((4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-1-[2-(4-methoxy-benzyloxy)-ethyl]-but-2-enyloxy}-dimethyl-silane