{(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester

Base Information

Chemical Name:{(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester
CAS No.:270070-68-3
Molecular Formula:C₃₁H₄₂O₇Si
Molecular Weight:554.756
Hs Code.:

{(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester

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Chemical Property of {(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester

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Technology Process of {(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester

There total 1 articles about {(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester 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: 63.0%

: 103516-15-0
(2R,3R,4R,5S)-4-<(ethoxycarbonyl)methyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

: 58479-61-1
tert-butylchlorodiphenylsilane

: (3aR,4aS,5R,8aR,8bR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-8a-vinyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyran-7-one

: 270070-68-3
{(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester

Guidance literature:: (2R,3R,4R,5S)-4-<(ethoxycarbonyl)methyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran; With acetic acid;

tert-butylchlorodiphenylsilane; With dmap; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4039(00)00013-7

Reference yield:

: 270070-68-3
{(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester

: (3R,4S,5S)-5-Benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-2-methoxymethoxy-5-methyl-cyclopent-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 28 steps

1: pyridine

2: 100 percent / aq. KOH / methanol

3: NaBH₄ / 2-methyl-propan-2-ol; methanol / Heating

4: Et₃N; DMAP / CH₂Cl₂

5: NaH / tetrahydrofuran

6: n-Bu₄NF / tetrahydrofuran

7: pyridine

8: O₃; Ph₃P / methanol / -78 °C

9: NaBH₄ / methanol

10: 2,6-lutidine / CH₂Cl₂

11: DIBAL-H / CH₂Cl₂ / -78 °C

12: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

13: NaClO₂; aq. NH₂SO₃H; aq. Na₂HPO₄ / 2-methyl-propan-2-ol

14: diethyl ether; CH₂Cl₂ / 0 °C

15: potassium hexamethyldisilazide / tetrahydrofuran / -78 °C

16: DMAP / pyridine

17: AcOH; H₂O / tetrahydrofuran

18: pyridine

19: 92 percent / aq. TFA / 0 °C

20: NaIO₄ / methanol; H₂O

21: BF₃*Et₂O / CH₂Cl₂ / 0 °C

22: MeOH; NEt₃

23: Raney Ni T-4 / acetone / Heating

24: 2,6-lutidine / CH₂Cl₂

25: aq. NH₃ / methanol

26: iPr₂NEt / CHCl₃

27: NaOMe / methanol

28: TfOH / CH₂Cl₂ / 0 °C

With pyridine; 2,6-dimethylpyridine; methanol; dmap; potassium hydroxide; ammonium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; oxalyl dichloride; trifluorormethanesulfonic acid; Raney Ni T-4; boron trifluoride diethyl etherate; aminosulfonic acid; tetrabutyl ammonium fluoride; water; sodium methylate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; water; acetone; tert-butyl alcohol; 1: Condensation / 2: cyclocondensation / 3: Reduction / 4: silylation / 5: Methylation / 6: desilylation / 7: Acylation / 8: ozonolysis / 9: Reduction / 10: silylation / 11: deesterification / 12: Oxidation / 13: Oxidation / 14: Methylation / 15: Dieckmann cyclization / 16: Acylation / 17: Hydrolysis / 18: Acetylation / 19: Hydrolysis / 20: Ring cleavage / 21: dithioacetalization / 22: methanolysis / 23: Elimination / 24: silylation / 25: Hydrolysis / 26: Etherification / 27: Deacetylation / 28:;
DOI:10.1016/S0040-4039(00)00013-7

Reference yield:

: 270070-68-3
{(3aR,5S,6R,6aR)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl}-acetic acid ethyl ester

: 270070-71-8
(3aR,4aS,5S,8aR,8bR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-8a-vinyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-c]pyran-7-one

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine

2: 100 percent / aq. KOH / methanol

With pyridine; potassium hydroxide; In methanol; 1: Condensation / 2: cyclocondensation;
DOI:10.1016/S0040-4039(00)00013-7