2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol

Base Information

• Chemical Name: 2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol
• CAS No.: 312487-82-4
• Molecular Formula: C₃₇H₅₈O₆Si
• Molecular Weight: 626.949
• Mol file: 312487-82-4.mol

Synonyms:

Chemical Property of 2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol

There total 31 articles about 2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol 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:

[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2,9a-dimethyl-2-vinyl-octahydro-1,5-dioxa-benzocyclohepten-3-yloxy]-tert-butyl-dimethyl-silane → 2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol (312487-82-4)

Guidance literature:

[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2,9a-dimethyl-2-vinyl-octahydro-1,5-dioxa-benzocyclohepten-3-yloxy]-tert-butyl-dimethyl-silane; With borane-THF; In tetrahydrofuran; at 0 - 25 ℃;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)01340-X

Reference yield:

(2R,3S,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-6-methyl-tetrahydro-pyran-3-ol (174198-73-3) → 2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol (312487-82-4)

Guidance literature:

Multi-step reaction with 31 steps

1.1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

2.1: imidazole / dimethylformamide / 25 °C

3.1: K₂CO₃ / methanol / 25 °C

4.1: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

5.1: LDA / tetrahydrofuran / -78 °C

6.1: TBAF / tetrahydrofuran / 25 °C

7.1: LiOH / H₂O; tetrahydrofuran / 0 °C

8.1: pyridine / 25 °C

9.1: 88 percent / DBU / benzene / 25 °C

10.1: 89 percent / diethyl ether / 0 °C

11.1: LiAlH₄ / diethyl ether / 0 - 25 °C

12.1: n-Bu₄NI; NaH / tetrahydrofuran / 0 - 25 °C

13.1: CSA / methanol / 25 °C

14.1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

15.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

16.1: Zn(AcO)2 / triethylamine; acetic acid; 2,2,4-trimethyl-pentane / reflux

17.1: K₂CO₃ / methanol / 25 °C

18.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

19.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

20.1: dimethylsulfoxide / 35 °C

21.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

22.1: DIBAH / CH₂Cl₂ / -78 °C

23.1: toluene / 100 °C

24.1: 93 percent / DIBAH / toluene / -78 °C

25.1: 85 percent / t-BuOOH; (-)-DIPT; Ti(i-PrO)4,MS-4 Angstroem / CH₂Cl₂ / -20 °C

26.1: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

27.1: NaHMDS / tetrahydrofuran / 0 °C

28.1: TBAF / tetrahydrofuran / 25 °C

29.1: PPTS / CH₂Cl₂ / 0 °C

30.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

31.1: BH₃*THF / tetrahydrofuran / 0 - 25 °C

31.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; tert.-butylhydroperoxide; lithium hydroxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; MS-4 Angstroem; Ti(i-PrO)4,MS-4 Angstroem; zinc diacetate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; toluene; benzene; 1.1: Acetylation / 2.1: silylation / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Addition / 6.1: ether cleavage / 7.1: Hydrolysis / 8.1: Cyclization / 9.1: Elimination / 10.1: Addition / 11.1: Reduction / 12.1: Alkylation / 13.1: Hydrolysis / 14.1: Acetylation / 15.1: Acylation / 16.1: ring-expansion / 17.1: Hydrolysis / 18.1: Acylation / 19.1: silylation / 20.1: Substitution / 21.1: silylation / 22.1: Reduction / 23.1: Condensation / 24.1: Reduction / 25.1: Epoxidation / 26.1: Oxidation / 27.1: Con;

DOI:10.1016/S0040-4039(00)01340-X

Reference yield:

(4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methyl-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b]pyran-2-one (312487-61-9) → 2-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-yl]-ethanol (312487-82-4)

Guidance literature:

Multi-step reaction with 22 steps

1.1: 89 percent / diethyl ether / 0 °C

2.1: LiAlH₄ / diethyl ether / 0 - 25 °C

3.1: n-Bu₄NI; NaH / tetrahydrofuran / 0 - 25 °C

4.1: CSA / methanol / 25 °C

5.1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

7.1: Zn(AcO)2 / triethylamine; acetic acid; 2,2,4-trimethyl-pentane / reflux

8.1: K₂CO₃ / methanol / 25 °C

9.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

10.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

11.1: dimethylsulfoxide / 35 °C

12.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

13.1: DIBAH / CH₂Cl₂ / -78 °C

14.1: toluene / 100 °C

15.1: 93 percent / DIBAH / toluene / -78 °C

16.1: 85 percent / t-BuOOH; (-)-DIPT; Ti(i-PrO)4,MS-4 Angstroem / CH₂Cl₂ / -20 °C

17.1: TPAP; NMO; MS-4 Angstroem / CH₂Cl₂ / 25 °C

18.1: NaHMDS / tetrahydrofuran / 0 °C

19.1: TBAF / tetrahydrofuran / 25 °C

20.1: PPTS / CH₂Cl₂ / 0 °C

21.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

22.1: BH₃*THF / tetrahydrofuran / 0 - 25 °C

22.2: NaOH; H₂O₂ / tetrahydrofuran; H₂O

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; tert.-butylhydroperoxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; MS-4 Angstroem; Ti(i-PrO)4,MS-4 Angstroem; zinc diacetate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; acetic acid; dimethyl sulfoxide; triethylamine; toluene; 1.1: Addition / 2.1: Reduction / 3.1: Alkylation / 4.1: Hydrolysis / 5.1: Acetylation / 6.1: Acylation / 7.1: ring-expansion / 8.1: Hydrolysis / 9.1: Acylation / 10.1: silylation / 11.1: Substitution / 12.1: silylation / 13.1: Reduction / 14.1: Condensation / 15.1: Reduction / 16.1: Epoxidation / 17.1: Oxidation / 18.1: Condensation / 19.1: ether cleavage / 20.1: Cyclization / 21.1: silylation / 22.1: Addition / 22.2: Oxidation;

DOI:10.1016/S0040-4039(00)01340-X

upstream raw materials:

(2R,3S,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-6-methyl-tetrahydro-pyran-3-ol

(4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-6-methyl-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b]pyran-2-one

(4R,4aR,6S,8aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4,6-dimethyl-hexahydro-pyrano[3,2-b]pyran-2-one

Acetic acid (4aS,6S,8aS)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-2-oxo-octahydro-pyrano[3,2-b]pyran-4-yl ester

Downstream raw materials:

{(2R,3R)-3-[(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-2-ylmethyl]-2-methyl-oxiranyl}-methanol

(2S,3R,4aS,6R,7S,9aR)-7-Benzyloxy-6-((R)-3-benzyloxy-1-methyl-propyl)-2-((2R,3R)-3-hydroxymethyl-3-methyl-oxiranylmethyl)-2,9a-dimethyl-octahydro-1,5-dioxa-benzocyclohepten-3-ol