(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

Base Information

• Chemical Name: (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene
• CAS No.: 816455-25-1
• Molecular Formula: C₂₄H₃₀O₃Si
• Molecular Weight: 394.586
• Mol file: 816455-25-1.mol

Synonyms:(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

Chemical Property of (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

There total 12 articles about (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene 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: 86.0%

(1S,2R,3S,4R,5R,6R)-5-Bromo-6-[(1S,2S,3R,4R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethoxy]-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde → (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene (816455-25-1)

Guidance literature:

(1S,2R,3S,4R,5R,6R)-5-Bromo-6-[(1S,2S,3R,4R)-3-(tert-butyl-diphenyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethoxy]-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde; With zinc trifluoromethanesulfonate; In N,N-dimethyl acetamide; at 40 ℃; for 0.5h;

With zinc; In N,N-dimethyl acetamide; at 70 ℃; for 5h;

DOI:10.1002/chem.200400444

Reference yield:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene (816455-25-1)

Guidance literature:

Multi-step reaction with 5 steps

1: LiAlH₄ / tetrahydrofuran / 20 h / 0 °C

2: 2.92 g / pyridine / 17 h / 20 °C

3: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 °C

4: imidazole / dimethylformamide / 23 h / 0 °C

5: 1.90 g / NaOMe / methanol / 2 h / 20 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; Lipase PS (Amano); water; sodium methylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo048566j

Reference yield:

Acetic acid (1R,2R,3S,4S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester → (1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene (816455-25-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jo048566j

upstream raw materials:

exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene

(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

(1S,2S,3R,4R)-2-acetoxymethyl-3-(1-ethoxyethoxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

Downstream raw materials:

(1S,2S,3R,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-(p-toluenesulfonyloxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene

(1R,6S,7R,8S)-7-(furan-2-carbonyl)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene

(1S,2S,3S,4R)-2-(tert-butyldiphenylsilyloxy)methyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene

(1R,6S,7S,8R)-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene