3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester

Base Information

Chemical Name:3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester
CAS No.:261776-51-6
Molecular Formula:C₆₄H₈₂O₁₀Si₂
Molecular Weight:1067.52
Hs Code.:

3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2<i>H</i>-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(<i>tert</i>-butyl-diphenyl-silanyloxy)-7-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid <i>tert</i>-butyl ester

Synonyms:3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester

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Chemical Property of 3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester

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Technology Process of 3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester

There total 16 articles about 3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl 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: 91.0%

: 261776-50-5
3-[4-benzyloxy-3-(4-methoxy-benzyloxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl]-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester

: 261776-51-6
3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane;
DOI:10.1039/a903063h

Reference yield:

: 13265-84-4
D-glucal

: 261776-51-6
3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: pyridine

2: NaH / dimethylformamide / 0 - 20 °C

3: NBS; H₂O / tetrahydrofuran

4: KHMDS; 18-crown-6 / toluene / 4 h / -75 - 0 °C

5: 0 - 20 °C

6: 93 percent / NaH / 0 - 20 °C

7: 94 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂

8: PPTS / CH₂Cl₂

9: DIBAL-H / CH₂Cl₂ / -78 - -20 °C

10: 82 percent / I₂; PPh₃; imidazole / toluene

11: LDA; DMPU / tetrahydrofuran / -78 - 0 °C

12: PPTS; MeOH

13: imidazole / dimethylformamide

14: 91 percent / DDQ; H₂O / 1,2-dichloro-ethane

With pyridine; 1H-imidazole; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-Bromosuccinimide; 18-crown-6 ether; water; iodine; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 1: Cyclization / 2: Etherification / 3: Addition / 4: Dehydrobromination / 5: Addition / 6: Etherification / 7: Cyclization / 8: Etherification / 9: Ring cleavage / 10: Substitution / 11: Alkylation / 12: Ring cleavage / 13: Etherification / 14: Reduction;
DOI:10.1039/a903063h

Reference yield:

: 365569-74-0
(4R,4aS,10aR)-6,6,8,8-Tetraisopropyl-4,4a,10,10a-tetrahydro-1,5,7,9-tetraoxa-6,8-disila-benzocycloocten-4-ol

: 261776-51-6
3-(4-benzyloxy-3-hydroxy-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl)-2-[6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: NaH / dimethylformamide / 0 - 20 °C

2: NBS; H₂O / tetrahydrofuran

3: KHMDS; 18-crown-6 / toluene / 4 h / -75 - 0 °C

4: 0 - 20 °C

5: 93 percent / NaH / 0 - 20 °C

6: 94 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂

7: PPTS / CH₂Cl₂

8: DIBAL-H / CH₂Cl₂ / -78 - -20 °C

9: 82 percent / I₂; PPh₃; imidazole / toluene

10: LDA; DMPU / tetrahydrofuran / -78 - 0 °C

11: PPTS; MeOH

12: imidazole / dimethylformamide

13: 91 percent / DDQ; H₂O / 1,2-dichloro-ethane

With 1H-imidazole; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-Bromosuccinimide; 18-crown-6 ether; water; iodine; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Addition / 3: Dehydrobromination / 4: Addition / 5: Etherification / 6: Cyclization / 7: Etherification / 8: Ring cleavage / 9: Substitution / 10: Alkylation / 11: Ring cleavage / 12: Etherification / 13: Reduction;
DOI:10.1039/a903063h