(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

Base Information

Chemical Name:(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one
CAS No.:244770-87-4
Molecular Formula:C₆₀H₇₂O₉Si₂
Molecular Weight:993.397
Hs Code.:

(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

Synonyms:(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

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Chemical Property of (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

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Technology Process of (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

There total 17 articles about (3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one 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: 80.0%

: 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

: 244770-87-4
(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

Guidance literature:: With camphor-10-sulfonic acid; In toluene; at 80 ℃;
DOI:10.1039/a903063h

Reference yield:

: 13265-84-4
D-glucal

: 244770-87-4
(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

Guidance literature:: Multi-step reaction with 15 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

15: 80 percent / CSA / toluene / 80 °C

With pyridine; 1H-imidazole; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-Bromosuccinimide; 18-crown-6 ether; camphor-10-sulfonic acid; 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 / 15: Cyclization;
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

: 244770-87-4
(3S,4aR,5aS,10aS,11R,11aR)-11-Benzyloxy-3-[(2S,3R,6S,7R)-6-(tert-butyl-diphenyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinyl-oxepan-3-yloxy]-4,4a,5a,6,9,10a,11,11a-octahydro-3H-1,5,10-trioxa-cyclohepta[b]naphthalen-2-one

Guidance literature:: Multi-step reaction with 14 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

14: 80 percent / CSA / toluene / 80 °C

With 1H-imidazole; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-Bromosuccinimide; 18-crown-6 ether; camphor-10-sulfonic acid; 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 / 14: Cyclization;
DOI:10.1039/a903063h