(3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene

Base Information

Chemical Name:(3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene
CAS No.:306769-38-0
Molecular Formula:C₃₇H₅₈O₄Si
Molecular Weight:594.951
Hs Code.:

Synonyms:(3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene

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Chemical Property of (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene

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Technology Process of (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene

There total 15 articles about (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene 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:

: 228252-17-3
(Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal

: 306769-38-0
(3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene

Guidance literature:: Multi-step reaction with 14 steps

1.1: CrCl₂ / dioxane; tetrahydrofuran / 0.5 h / 22 °C

2.1: 268 mg / APTS / methanol / 0.5 h / 22 °C

3.1: 74 percent / (MeCN)2PdCl₂ / dimethylformamide / 2 h / 22 °C

4.1: 92 percent / (Cl₃C)2CO; PPh₃ / tetrahydrofuran / 0.67 h / 22 °C

5.1: 749 mg / Cs₂CO₃; CsI / acetone / 15 h / 60 °C

6.1: 72 percent / LiI*2H₂O; 2,4,6-collidine / 15 h / 100 °C

7.1: NaI; 15-crown-5 ether / CH₂Cl₂ / 0.08 h / 22 °C

7.2: bromomethylborane / CH₂Cl₂; diethyl ether / -78 - 22 °C

7.3: dimethylformamide; CH₂Cl₂; diethyl ether / 6 h / 55 °C

8.1: 330 mg / K₂CO₃ / methanol / 15 h / 22 °C

9.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 22 °C

10.1: 81 percent / Et₃N / toluene / 30 h / 220 °C

11.1: KHMDS / tetrahydrofuran; toluene / 0.58 h / -78 - 0 °C

11.2: 95 percent / tetrahydrofuran; toluene / 2.08 h / -78 - 0 °C

12.1: m-CPBA; Li₂CO₃ / CH₂Cl₂ / 3 h / -78 °C

13.1: APTS / CH₂Cl₂ / 2.75 h / 0 °C

13.2: 3.9 mg / sodium borohydride / ethanol / 3 h / 0 °C

14.1: NaH; n-Bu₄NI / tetrahydrofuran; dimethylformamide / 6 h / 22 °C

With 2,4,6-trimethyl-pyridine; chromium dichloride; isocyanate de chlorosulfonyle; 15-crown-5; 1,1,1,3,3,3-hexachloro-propan-2-one; tetra-(n-butyl)ammonium iodide; lithium carbonate; potassium hexamethylsilazane; sodium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; sodium iodide; lithium iodide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Takai homologation / 2.1: Desilylation / 3.1: Stille coupling / 4.1: Substitution / 5.1: Cyclization / 6.1: Decarboxylation / 7.1: Substitution / 7.2: Substitution / 7.3: Acetoxylation / 8.1: Deacetylation / 9.1: Dess-Martin oxidation / 10.1: Tandem transannular Diels-Alder-aldol reaction / 11.1: Wittig reaction / 11.2: Wittig reaction / 12.1: Epoxidation / 13.1: Addition / 13.2: Reduction / 14.1: Benzylation;
DOI:10.1021/jo0007635

Reference yield:

: 228252-15-1
(Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-N-methoxy-7-methoxymethyl-N,2,6-trimethyl-3-(triisopropylsilyl)oxy-6-octenamide

: 306769-38-0
(3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene

Guidance literature:: Multi-step reaction with 15 steps

1.1: DIBALH / tetrahydrofuran; toluene / 1 h / -78 °C

2.1: CrCl₂ / dioxane; tetrahydrofuran / 0.5 h / 22 °C

3.1: 268 mg / APTS / methanol / 0.5 h / 22 °C

4.1: 74 percent / (MeCN)2PdCl₂ / dimethylformamide / 2 h / 22 °C

5.1: 92 percent / (Cl₃C)2CO; PPh₃ / tetrahydrofuran / 0.67 h / 22 °C

6.1: 749 mg / Cs₂CO₃; CsI / acetone / 15 h / 60 °C

7.1: 72 percent / LiI*2H₂O; 2,4,6-collidine / 15 h / 100 °C

8.1: NaI; 15-crown-5 ether / CH₂Cl₂ / 0.08 h / 22 °C

8.2: bromomethylborane / CH₂Cl₂; diethyl ether / -78 - 22 °C

8.3: dimethylformamide; CH₂Cl₂; diethyl ether / 6 h / 55 °C

9.1: 330 mg / K₂CO₃ / methanol / 15 h / 22 °C

10.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 22 °C

11.1: 81 percent / Et₃N / toluene / 30 h / 220 °C

12.1: KHMDS / tetrahydrofuran; toluene / 0.58 h / -78 - 0 °C

12.2: 95 percent / tetrahydrofuran; toluene / 2.08 h / -78 - 0 °C

13.1: m-CPBA; Li₂CO₃ / CH₂Cl₂ / 3 h / -78 °C

14.1: APTS / CH₂Cl₂ / 2.75 h / 0 °C

14.2: 3.9 mg / sodium borohydride / ethanol / 3 h / 0 °C

15.1: NaH; n-Bu₄NI / tetrahydrofuran; dimethylformamide / 6 h / 22 °C

With 2,4,6-trimethyl-pyridine; chromium dichloride; isocyanate de chlorosulfonyle; 15-crown-5; 1,1,1,3,3,3-hexachloro-propan-2-one; tetra-(n-butyl)ammonium iodide; lithium carbonate; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; sodium iodide; lithium iodide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Reduction / 2.1: Takai homologation / 3.1: Desilylation / 4.1: Stille coupling / 5.1: Substitution / 6.1: Cyclization / 7.1: Decarboxylation / 8.1: Substitution / 8.2: Substitution / 8.3: Acetoxylation / 9.1: Deacetylation / 10.1: Dess-Martin oxidation / 11.1: Tandem transannular Diels-Alder-aldol reaction / 12.1: Wittig reaction / 12.2: Wittig reaction / 13.1: Epoxidation / 14.1: Addition / 14.2: Reduction / 15.1: Benzylation;
DOI:10.1021/jo0007635

Reference yield:

: 263155-35-7
(2E,8E)-(6S,7S)-3,7-dimethyl-9-iodo-2-methoxymethyl-6-(triisopropylsilyloxy)nona-2,8-dien-1-ol

: 306769-38-0
(3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene

Guidance literature:: Multi-step reaction with 12 steps

1.1: 74 percent / (MeCN)2PdCl₂ / dimethylformamide / 2 h / 22 °C

2.1: 92 percent / (Cl₃C)2CO; PPh₃ / tetrahydrofuran / 0.67 h / 22 °C

3.1: 749 mg / Cs₂CO₃; CsI / acetone / 15 h / 60 °C

4.1: 72 percent / LiI*2H₂O; 2,4,6-collidine / 15 h / 100 °C

5.1: NaI; 15-crown-5 ether / CH₂Cl₂ / 0.08 h / 22 °C

5.2: bromomethylborane / CH₂Cl₂; diethyl ether / -78 - 22 °C

5.3: dimethylformamide; CH₂Cl₂; diethyl ether / 6 h / 55 °C

6.1: 330 mg / K₂CO₃ / methanol / 15 h / 22 °C

7.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 22 °C

8.1: 81 percent / Et₃N / toluene / 30 h / 220 °C

9.1: KHMDS / tetrahydrofuran; toluene / 0.58 h / -78 - 0 °C

9.2: 95 percent / tetrahydrofuran; toluene / 2.08 h / -78 - 0 °C

10.1: m-CPBA; Li₂CO₃ / CH₂Cl₂ / 3 h / -78 °C

11.1: APTS / CH₂Cl₂ / 2.75 h / 0 °C

11.2: 3.9 mg / sodium borohydride / ethanol / 3 h / 0 °C

12.1: NaH; n-Bu₄NI / tetrahydrofuran; dimethylformamide / 6 h / 22 °C

With 2,4,6-trimethyl-pyridine; isocyanate de chlorosulfonyle; 15-crown-5; 1,1,1,3,3,3-hexachloro-propan-2-one; tetra-(n-butyl)ammonium iodide; lithium carbonate; potassium hexamethylsilazane; sodium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; sodium iodide; lithium iodide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Stille coupling / 2.1: Substitution / 3.1: Cyclization / 4.1: Decarboxylation / 5.1: Substitution / 5.2: Substitution / 5.3: Acetoxylation / 6.1: Deacetylation / 7.1: Dess-Martin oxidation / 8.1: Tandem transannular Diels-Alder-aldol reaction / 9.1: Wittig reaction / 9.2: Wittig reaction / 10.1: Epoxidation / 11.1: Addition / 11.2: Reduction / 12.1: Benzylation;
DOI:10.1021/jo0007635