(3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene

Base Information

• Chemical Name: (3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene
• CAS No.: 696574-71-7
• Molecular Formula: C₂₆H₄₀O₇Si
• Molecular Weight: 492.685
• Mol file: 696574-71-7.mol

Synonyms:(3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene

Chemical Property of (3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene

There total 6 articles about (3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-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: 98.0%

benzoyl chloride (98-88-4) + (3R,4S,5R)-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene-1-methanol (696574-73-9) → (3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene (696574-71-7)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 1h;

DOI:10.1007/s11696-016-0004-8

Reference yield:

methyl shikimate (40983-58-2) → (3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene (696574-71-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / (+/-)-camphorsulfonic acid / methanol / 48 h / 90 °C

2: 97 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

3: 92 percent / diisobutylaluminium hydride / toluene / 0.33 h / -78 °C / d

4: 97 percent / 4-(dimethylamino)pyridine; pyridine / 2.33 h / 20 °C

With pyridine; 1H-imidazole; dmap; camphor-10-sulfonic acid; diisobutylaluminium hydride; In methanol; dichloromethane; toluene;

DOI:10.1016/j.tet.2004.02.066

Reference yield:

methyl (3R,4S,5R)-3-hydroxy-4,5-<(2S,3S)-2,3-dimethoxybutan-2,3-dioxy>-cyclohex-1-en-1-carboxylate (245054-32-4) → (3R,4S,5R)-1-benzoyloxymethyl-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene (696574-71-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 20 °C

2: 92 percent / diisobutylaluminium hydride / toluene / 0.33 h / -78 °C / d

3: 97 percent / 4-(dimethylamino)pyridine; pyridine / 2.33 h / 20 °C

With pyridine; 1H-imidazole; dmap; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1016/j.tet.2004.02.066

upstream raw materials:

benzoyl chloride

(3R,4S,5R)-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohex-1-ene-1-methanol

methyl shikimate

tert-butyldimethylsilyl chloride

Downstream raw materials:

(1R,2R,3S)-1-benzoyloxymethyl-1,2-O,O-isopropylidene-3-hydroxy-cyclohex-4-ene

(1R,2R,3R,4S,5R)-1-benzoyloxymethyl-1,2-dihydroxy-3-O-(tert-butyldimethylsilyl)-4,5-(2,3-dimethoxybutane-2,3-dioxy)-cyclohexane