(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol

Base Information

Chemical Name:(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol
CAS No.:126694-04-0
Molecular Formula:C₃₅H₅₀O₇
Molecular Weight:582.778
Hs Code.:

(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol

Synonyms:(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol

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Chemical Property of (2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol

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Technology Process of (2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol

There total 32 articles about (2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol 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:

: 126693-99-0
(Z)-(5aS,6aR,8S,12aS,13aR)-4,6a,8-Trimethyl-5,5a,6a,7,8,12a,13,13a-octahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-2,11-dione

: 126694-04-0
(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / H₂ / 10 percent Pd/C / ethyl acetate; CH₂Cl₂ / 3.5 h / 25 °C

2: 63 percent / Lawesson's reagent, tetramethylthiourea / xylene / 3 h / 115 °C

4: 1.) thexylborane, 2.) H₂O₂, NaOH, H₂O / 1.) THF, 0 deg C, 5 h, 2.) THF, 0 deg C to 25 deg C, 2 h

With Lawessons reagent; sodium hydroxide; 1,1,3,3-tetramethyl-2-thiourea; thexylborane; water; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In dichloromethane; ethyl acetate; xylene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

Reference yield:

: 126693-95-6
(S)-3-[(2R,3S,5R,6S)-3,5-Bis-benzyloxy-2-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-2-methyl-propionaldehyde

: 126694-04-0
(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol

Guidance literature:: Multi-step reaction with 11 steps

1: 81 percent / ZnBr₂ / diethyl ether / 0.33 h / -78 °C

2: H₂ / 20 percent Pd(OH)2/C / tetrahydrofuran / 3 h / 25 °C

3: 1.) dipyridyl disulfide, Ph₃P, 2.) AgClO₄ / 1.) CH₂Cl₂, 25 deg C, 1 h, 2.) toluene, 110 deg C, 2 h

4: 85 percent / HF*pyr / tetrahydrofuran / 3 h / 25 °C

5: 87 percent / 3)2O>2SPh₂ / CH₂Cl₂ / 0.5 h / 0 °C

6: 92 percent / HF*pyr / tetrahydrofuran / 4 h / 25 °C

7: 92 percent / 3)2O>2SPh₂ / CH₂Cl₂ / 0.5 h / 0 °C

8: 100 percent / H₂ / 10 percent Pd/C / ethyl acetate; CH₂Cl₂ / 3.5 h / 25 °C

9: 63 percent / Lawesson's reagent, tetramethylthiourea / xylene / 3 h / 115 °C

11: 1.) thexylborane, 2.) H₂O₂, NaOH, H₂O / 1.) THF, 0 deg C, 5 h, 2.) THF, 0 deg C to 25 deg C, 2 h

With Lawessons reagent; sodium hydroxide; 2,2'-dipyridyldisulphide; 1,1,3,3-tetramethyl-2-thiourea; 2SPh2; thexylborane; water; hydrogen; dihydrogen peroxide; silver perchlorate; pyridine hydrogenfluoride; triphenylphosphine; zinc dibromide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; xylene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N

Reference yield:

: 126693-98-9,126785-21-5,126785-22-6,126785-23-7
(5aS,6aR,8S,12aS,13aR)-4,9-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6a,8-trimethyl-dodecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-2,11-dione

: 126694-04-0
(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-3,10-diol

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / HF*pyr / tetrahydrofuran / 3 h / 25 °C

2: 87 percent / 3)2O>2SPh₂ / CH₂Cl₂ / 0.5 h / 0 °C

3: 92 percent / HF*pyr / tetrahydrofuran / 4 h / 25 °C

4: 92 percent / 3)2O>2SPh₂ / CH₂Cl₂ / 0.5 h / 0 °C

5: 100 percent / H₂ / 10 percent Pd/C / ethyl acetate; CH₂Cl₂ / 3.5 h / 25 °C

6: 63 percent / Lawesson's reagent, tetramethylthiourea / xylene / 3 h / 115 °C

8: 1.) thexylborane, 2.) H₂O₂, NaOH, H₂O / 1.) THF, 0 deg C, 5 h, 2.) THF, 0 deg C to 25 deg C, 2 h

With Lawessons reagent; sodium hydroxide; 1,1,3,3-tetramethyl-2-thiourea; 2SPh2; thexylborane; water; hydrogen; dihydrogen peroxide; pyridine hydrogenfluoride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; xylene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<599::AID-CHEM599>3.0.CO;2-N