(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

Base Information

Chemical Name:(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
CAS No.:1055029-85-0
Molecular Formula:C₃₄H₄₈O₇
Molecular Weight:568.751
Hs Code.:

(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

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Chemical Property of (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

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Technology Process of (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

There total 36 articles about (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 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:

: 312487-77-7
{(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

: 1055029-85-0
(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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 40 ℃;
DOI:10.1016/S0040-4039(00)01340-X

Reference yield:

: 174198-73-3
(2R,3S,6S)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-hydroxymethyl-6-methyl-tetrahydro-pyran-3-ol

: 1055029-85-0
(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

Guidance literature:: Multi-step reaction with 36 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

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

33.1: toluene / 100 °C

34.1: 87 percent / DIBAH / toluene / -78 °C

35.1: 93 percent / MCPBA / CH₂Cl₂ / 0 °C

36.1: TBAF / tetrahydrofuran / 40 °C

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; 3-chloro-benzenecarboperoxoic acid; 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:

: 312487-61-9
(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

: 1055029-85-0
(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

Guidance literature:: Multi-step reaction with 27 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

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

24.1: toluene / 100 °C

25.1: 87 percent / DIBAH / toluene / -78 °C

26.1: 93 percent / MCPBA / CH₂Cl₂ / 0 °C

27.1: TBAF / tetrahydrofuran / 40 °C

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; 3-chloro-benzenecarboperoxoic acid; 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 / 23.1: Oxidation / 24.1: Condensation / 25.1: Reduction / 26.1: Epo;
DOI:10.1016/S0040-4039(00)01340-X