(1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.0^2,6]undecan-8-one

Base Information

• Chemical Name: (1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.0^2,6]undecan-8-one
• CAS No.: 814920-04-2
• Molecular Formula: C₃₆H₆₀O₇Si₂
• Molecular Weight: 661.039

Synonyms:(1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.0^2,6]undecan-8-one

Chemical Property of (1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.0^2,6]undecan-8-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.0^2,6]undecan-8-one

There total 15 articles about (1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.0^2,6]undecan-8-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:

(1S,3R,7R,8S,9R,10S,11S)-9-Benzyloxymethyl-10-hydroxymethyl-11-methyl-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one (312923-90-3) → (1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.02,6]undecan-8-one (814920-04-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 29 percent / diacetoxyiodobenzene; iodine / CH₂Cl₂ / 0.83 h / 0 °C / Irradiation

2.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 10 h / 20 °C

3.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

3.2: 83 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

4.1: Zn(BH₄)2 / diethyl ether / 0.5 h / 0 °C

5.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

6.1: 2.25 g / PPTS / acetone / 14 h / 20 °C

7.1: LiHMDS; HMPA / tetrahydrofuran / 1.5 h / -78 °C

7.2: 86 percent / tetrahydrofuran / 0.92 h / -78 - -40 °C

8.1: O₃ / CH₂Cl₂ / 0.08 h / -78 °C

8.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

9.1: 197 mg / NaBH₄ / CH₂Cl₂; methanol / 0.08 h / 20 °C

10.1: 97 percent / n-Bu₃P / tetrahydrofuran / 1.67 h / -78 - 20 °C

11.1: 252 mg / H₂O₂ / tetrahydrofuran / 12 h / 20 °C

12.1: 335 mg / LiAlH₄ / dioxane / 0.02 h / Heating

13.1: 345 mg / Et₃N; DMAP / CH₂Cl₂ / 1.17 h / 20 °C

14.1: 93 percent / 4-methylmorpholine N-oxide / TPAP / acetonitrile / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; zinc(II) tetrahydroborate; tributylphosphine; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; acetone; acetonitrile; 11.1: Grieco olefination;

DOI:10.1021/jo048681u

Reference yield:

(1S,3R,7S,8S,9R,10R,11R)-9-Benzyloxymethyl-7,11-dihydroxy-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-4-oxa-tricyclo[5.3.1.03,8]undecan-5-one → (1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.02,6]undecan-8-one (814920-04-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 2.25 g / PPTS / acetone / 14 h / 20 °C

2.1: LiHMDS; HMPA / tetrahydrofuran / 1.5 h / -78 °C

2.2: 86 percent / tetrahydrofuran / 0.92 h / -78 - -40 °C

3.1: O₃ / CH₂Cl₂ / 0.08 h / -78 °C

3.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

4.1: 197 mg / NaBH₄ / CH₂Cl₂; methanol / 0.08 h / 20 °C

5.1: 97 percent / n-Bu₃P / tetrahydrofuran / 1.67 h / -78 - 20 °C

6.1: 252 mg / H₂O₂ / tetrahydrofuran / 12 h / 20 °C

7.1: 335 mg / LiAlH₄ / dioxane / 0.02 h / Heating

8.1: 345 mg / Et₃N; DMAP / CH₂Cl₂ / 1.17 h / 20 °C

9.1: 93 percent / 4-methylmorpholine N-oxide / TPAP / acetonitrile / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; tributylphosphine; dihydrogen peroxide; pyridinium p-toluenesulfonate; ozone; 4-methylmorpholine N-oxide; triethylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetone; acetonitrile; 6.1: Grieco olefination;

DOI:10.1021/jo048681u

Reference yield:

C28H42O7Si (814919-99-8) → (1S,2R,6S,7R,10R,11R)-11-Benzyloxymethyl-6-[(S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-4,4-dimethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.02,6]undecan-8-one (814920-04-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: LiHMDS; HMPA / tetrahydrofuran / 1.5 h / -78 °C

1.2: 86 percent / tetrahydrofuran / 0.92 h / -78 - -40 °C

2.1: O₃ / CH₂Cl₂ / 0.08 h / -78 °C

2.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

3.1: 197 mg / NaBH₄ / CH₂Cl₂; methanol / 0.08 h / 20 °C

4.1: 97 percent / n-Bu₃P / tetrahydrofuran / 1.67 h / -78 - 20 °C

5.1: 252 mg / H₂O₂ / tetrahydrofuran / 12 h / 20 °C

6.1: 335 mg / LiAlH₄ / dioxane / 0.02 h / Heating

7.1: 345 mg / Et₃N; DMAP / CH₂Cl₂ / 1.17 h / 20 °C

8.1: 93 percent / 4-methylmorpholine N-oxide / TPAP / acetonitrile / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; tributylphosphine; dihydrogen peroxide; ozone; 4-methylmorpholine N-oxide; triethylamine; lithium hexamethyldisilazane; tetrapropylammonium perruthennate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile; 5.1: Grieco olefination;

DOI:10.1021/jo048681u

upstream raw materials:

C₂₈H₄₂O₇Si

(1S,3R,7S,8S,9R,10R)-9-Benzyloxymethyl-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecane-5,11-dione

C₃₀H₄₄O₇Si

(1S,3R,7S,8S,9R,10S)-9-Benzyloxymethyl-11-methylene-10-(2-trimethylsilanyl-ethoxymethoxymethyl)-7-trimethylsilanyloxy-4-oxa-tricyclo[5.3.1.0^3,8]undecan-5-one

Downstream raw materials:

(S)-2-[(1R,2S,6R,7S,8R,9R)-9-Benzyloxymethyl-4,4-dimethyl-10-oxo-8-(2-trimethylsilanyl-ethoxymethoxymethyl)-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propionaldehyde

C₂₇H₃₆O₇

C₂₈H₃₈O₆

C₂₇H₃₈O₇

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