<1S-(1α,2α,3α,(S^*),4α)>-α-<2-<3-<oxy>propyl>phenyl>-7-oxabicyclo<2.2.1>heptane-2,3-dimethanol

Base Information

• Chemical Name: <1S-(1α,2α,3α,(S^*),4α)>-α-<2-<3-<oxy>propyl>phenyl>-7-oxabicyclo<2.2.1>heptane-2,3-dimethanol
• CAS No.: 135682-54-1
• Molecular Formula: C₂₅H₄₂O₄Si
• Molecular Weight: 434.692
• Mol file: 135682-54-1.mol

Synonyms:<1S-(1α,2α,3α,(S^*),4α)>-α-<2-<3-<oxy>propyl>phenyl>-7-oxabicyclo<2.2.1>heptane-2,3-dimethanol

Chemical Property of <1S-(1α,2α,3α,(S^*),4α)>-α-<2-<3-<oxy>propyl>phenyl>-7-oxabicyclo<2.2.1>heptane-2,3-dimethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1S-(1α,2α,3α,(S^*),4α)>-α-<2-<3-<oxy>propyl>phenyl>-7-oxabicyclo<2.2.1>heptane-2,3-dimethanol

There total 8 articles about <1S-(1α,2α,3α,(S^*),4α)>-α-<2-<3-<oxy>propyl>phenyl>-7-oxabicyclo<2.2.1>heptane-2,3-dimethanol 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: 5.0%

→ [1S-(1α,2α,3α,4α)]-α-[2-[3-[[Dimethyl-(1,1,2-trimethylpropyl)silyl]oxy]propyl]phenyl]-7-oxabicyclo[2.2.1]heptane-2,3-dimethanol (133027-57-3,133577-66-9,133644-93-6,135682-54-1,135682-66-5) + <1S-(1α,2α,3α,4α)>-2-<<3-<4-<<(4-cyclohexylbutyl)amino>thiomethyl>-2-oxazolyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester (142663-78-3)

Guidance literature:

Reference yield:

ortho-bromobenzaldehyde (6630-33-7) → [1S-(1α,2α,3α,4α)]-α-[2-[3-[[Dimethyl-(1,1,2-trimethylpropyl)silyl]oxy]propyl]phenyl]-7-oxabicyclo[2.2.1]heptane-2,3-dimethanol (133027-57-3,133577-66-9,133644-93-6,135682-54-1,135682-66-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / tetrahydrofuran / 18 h / 25 °C

2: 97 percent / H₂ / 5percent Rh/Al₂O₃ / methanol / 3 h

3: 100 percent / diisobutylaluminum hydride / toluene / 1.) -78 deg C, 2 h, 2.) from -78 deg C to 0 deg C, 2 h

4: 92 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 4 h / 25 °C

5: 1.) tert-butyllithium / 1.) ether, pentane, a) -100 deg C, 15 min, b) 0 deg C, 15 min, 2.) ether, pentane, THF, 0 deg C, 1 h

With dmap; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; Rh/Al₂O₃; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/jm00113a030

Reference yield:

methyl (2E)-3-(2-bromophenyl)-2-propenoate (102540-15-8,123100-53-8,92991-89-4) → [1S-(1α,2α,3α,4α)]-α-[2-[3-[[Dimethyl-(1,1,2-trimethylpropyl)silyl]oxy]propyl]phenyl]-7-oxabicyclo[2.2.1]heptane-2,3-dimethanol (133027-57-3,133577-66-9,133644-93-6,135682-54-1,135682-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / H₂ / 5percent Rh/Al₂O₃ / methanol / 3 h

2: 100 percent / diisobutylaluminum hydride / toluene / 1.) -78 deg C, 2 h, 2.) from -78 deg C to 0 deg C, 2 h

3: 92 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 4 h / 25 °C

4: 1.) tert-butyllithium / 1.) ether, pentane, a) -100 deg C, 15 min, b) 0 deg C, 15 min, 2.) ether, pentane, THF, 0 deg C, 1 h

With dmap; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; Rh/Al₂O₃; In methanol; dichloromethane; toluene;

DOI:10.1021/jm00113a030

upstream raw materials:

7-oxabicyclo<2.2.1>heptane tetrahydrofuranol

<3-(2-bromophenyl)propoxy>dimethyl(1,1,2-trimethylpropyl)silane

ortho-bromobenzaldehyde

3-(2-bromophenyl)propanoic acid,methyl ester

Downstream raw materials:

[(1R,2R,3R,4S)-3-(2-{3-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-propyl}-benzyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-methanol

anti-<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid

syn-<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid

<1S-1α,2α,3α,4α>-2-<<3-<<<(phenylamino)carbonyl>hydrazono>methyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenebutanoic acid