methyl <2S-<2α(4R),3β(Z),4β>>-7-<4-(tert-butyldiphenylsilyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydrofuran-3-yl>-5-heptenoate

Base Information

Chemical Name:methyl <2S-<2α(4R),3β(Z),4β>>-7-<4-(tert-butyldiphenylsilyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydrofuran-3-yl>-5-heptenoate
CAS No.:101069-30-1
Molecular Formula:C₃₃H₄₆O₆Si
Molecular Weight:566.81
Hs Code.:

Synonyms:

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Chemical Property of methyl <2S-<2α(4R),3β(Z),4β>>-7-<4-(tert-butyldiphenylsilyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydrofuran-3-yl>-5-heptenoate

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Technology Process of methyl <2S-<2α(4R),3β(Z),4β>>-7-<4-(tert-butyldiphenylsilyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydrofuran-3-yl>-5-heptenoate

There total 21 articles about methyl <2S-<2α(4R),3β(Z),4β>>-7-<4-(tert-butyldiphenylsilyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydrofuran-3-yl>-5-heptenoate 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:

: 101069-26-5
1,4-anhydro-2-O-tert-butyldiphenylsilyl-5,6-O-isopropylidene-D-glucitol

: 101069-30-1,101069-44-7
methyl <2S-<2α(4R),3β(Z),4β>>-7-<4-(tert-butyldiphenylsilyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydrofuran-3-yl>-5-heptenoate

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / 1-ethyl-3-(3'-dimethylaminopropyl)carbodi-imide hydrochloride, dichloroacetic acid / dimethylsulfoxide / 3 h / Ambient temperature

2: CH₂Cl₂ / 12 h / Ambient temperature

3: H₂ / 10percent Pd/C / ethanol / 16 h

4: 97 percent / 1.4 M di-isobutylaluminum hydride / toluene; hexane / 0.5 h / -78 °C

5: 1.) butyl-lithium, bis(trimethylsilyl)amine / 1.) hexane, ether, rt., 1 h 2.) hexamethylphosphoric triamide, rt., 40 h

6: diethyl ether / 6 h

With dichloro-acetic acid; n-butyllithium; diisobutylaluminum hydride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/S0008-6215(00)90454-3

Reference yield:

: 101125-99-9
1,4-anhydro-2-O-tert-butyldiphenylsilyl-5,6-O-isopropylidene-D-ribo-3-hexulose

: 101069-30-1,101069-44-7
methyl <2S-<2α(4R),3β(Z),4β>>-7-<4-(tert-butyldiphenylsilyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydrofuran-3-yl>-5-heptenoate

Guidance literature:: Multi-step reaction with 5 steps

1: CH₂Cl₂ / 12 h / Ambient temperature

2: H₂ / 10percent Pd/C / ethanol / 16 h

3: 97 percent / 1.4 M di-isobutylaluminum hydride / toluene; hexane / 0.5 h / -78 °C

4: 1.) butyl-lithium, bis(trimethylsilyl)amine / 1.) hexane, ether, rt., 1 h 2.) hexamethylphosphoric triamide, rt., 40 h

5: diethyl ether / 6 h

With n-butyllithium; diisobutylaluminum hydride; hydrogen; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In diethyl ether; ethanol; hexane; dichloromethane; toluene;
DOI:10.1016/S0008-6215(00)90454-3

Reference yield:

: 101069-27-6
1,4-anhydro-2-O-tert-butyldiphenylsilyl-3-deoxy-3-C-(ethoxycarbonylmethylene)-5,6-O-isopropylidene-D-ribo-hexitol

: 101069-30-1,101069-44-7
methyl <2S-<2α(4R),3β(Z),4β>>-7-<4-(tert-butyldiphenylsilyloxy)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-tetrahydrofuran-3-yl>-5-heptenoate

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / 10percent Pd/C / ethanol / 16 h

2: 97 percent / 1.4 M di-isobutylaluminum hydride / toluene; hexane / 0.5 h / -78 °C

3: 1.) butyl-lithium, bis(trimethylsilyl)amine / 1.) hexane, ether, rt., 1 h 2.) hexamethylphosphoric triamide, rt., 40 h

4: diethyl ether / 6 h

With n-butyllithium; diisobutylaluminum hydride; hydrogen; 1,1,1,3,3,3-hexamethyl-disilazane; palladium on activated charcoal; In diethyl ether; ethanol; hexane; toluene;
DOI:10.1016/S0008-6215(00)90454-3