(2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene

Base Information

Chemical Name:(2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene
CAS No.:870135-92-5
Molecular Formula:C₃₃H₄₆O₆
Molecular Weight:538.725
Hs Code.:

Synonyms:(2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene

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Chemical Property of (2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene

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Technology Process of (2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene

There total 29 articles about (2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene 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:

: (2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3-ethynyloxy-3,8a-dimethyl-6-pent-4-enyloxy-decahydro-1,8,10-trioxa-anthracene

: 870135-92-5
(2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene

Guidance literature:: With quinoline; Lindlar's catalyst; hydrogen; In ethyl acetate; at 20 ℃;
DOI:10.1002/anie.200501925

Reference yield:

: 870135-80-1
(2S,3S,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

: 870135-92-5
(2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene

Guidance literature:: Multi-step reaction with 22 steps

1.2: 88 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

2.1: n-BuLi; CuCN / tetrahydrofuran / -78 °C

2.2: 78 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 °C

3.1: KH / tetrahydrofuran

3.2: 88 percent / n-BuLi / diethyl ether / -78 - -40 °C

4.1: 85 percent / CuBr; LiBr / tetrahydrofuran / -95 - -78 °C

5.1: 84 percent / CuCn; LiCl / tetrahydrofuran / -78 °C

6.1: 89 percent / ruthenium complex / toluene / 70 °C

7.1: thexyl borane / tetrahydrofuran / 0 - 20 °C

7.2: 62 percent / NaBO₃*4H₂O; pH 7 buffer / tetrahydrofuran

8.1: 71 percent / TsOH / 20 °C

9.1: DMAP; Et₃N / CH₂Cl₂ / 20 °C

10.1: CAN / acetonitrile; H₂O / 20 °C

11.1: nBu₃P / tetrahydrofuran / 20 °C

12.1: H₂O₂; NaHCO₃ / tetrahydrofuran; H₂O / 40 °C

13.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

14.1: Dess-Martin periodinane / CH₂Cl₂ / 0 °C

15.1: toluene / -78 °C

16.1: HCl / tetrahydrofuran; H₂O / 60 °C

17.1: NaBH₄ / methanol / 0 °C

18.1: n-Bu₃P / tetrahydrofuran / 20 °C

19.1: H₂O₂; NaHCO₃ / tetrahydrofuran; H₂O / 40 °C

20.1: 66 percent / n-Bu₄N⁽¹⁺⁾*I^(1-) / tetrahydrofuran; dimethylformamide / Heating

21.1: tetrahydrofuran / 0 °C

21.2: n-BuLi / tetrahydrofuran; diethyl ether / -78 - -40 °C

22.1: H₂; Lindlar catalyst; quinoline / ethyl acetate / 20 °C

With quinoline; hydrogenchloride; dmap; sodium tetrahydroborate; Lindlar's catalyst; n-butyllithium; ammonium cerium(IV) nitrate; tributylphosphine; thexyl borane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; lithium chloride; copper(I) bromide; lithium bromide; ruthenium; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/anie.200501925

Reference yield:

: (1aS,2aR,6aR,7R,7aR)-7-Benzyloxy-5,5-di-tert-butyl-hexahydro-1,2,4,6-tetraoxa-5-sila-cyclopropa[b]naphthalene

: 870135-92-5
(2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2,7-Diallyl-9-benzyloxy-3,8a-dimethyl-6-pent-4-enyloxy-3-vinyloxy-decahydro-1,8,10-trioxa-anthracene

Guidance literature:: Multi-step reaction with 26 steps

1.1: tetrahydrofuran / 0 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: toluene / -78 °C

4.1: 98 percent / (HF)3*NEt₃ / tetrahydrofuran / 0 °C

5.2: 88 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

6.1: n-BuLi; CuCN / tetrahydrofuran / -78 °C

6.2: 78 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 °C

7.1: KH / tetrahydrofuran

7.2: 88 percent / n-BuLi / diethyl ether / -78 - -40 °C

8.1: 85 percent / CuBr; LiBr / tetrahydrofuran / -95 - -78 °C

9.1: 84 percent / CuCn; LiCl / tetrahydrofuran / -78 °C

10.1: 89 percent / ruthenium complex / toluene / 70 °C

11.1: thexyl borane / tetrahydrofuran / 0 - 20 °C

11.2: 62 percent / NaBO₃*4H₂O; pH 7 buffer / tetrahydrofuran

12.1: 71 percent / TsOH / 20 °C

13.1: DMAP; Et₃N / CH₂Cl₂ / 20 °C

14.1: CAN / acetonitrile; H₂O / 20 °C

15.1: nBu₃P / tetrahydrofuran / 20 °C

16.1: H₂O₂; NaHCO₃ / tetrahydrofuran; H₂O / 40 °C

17.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

18.1: Dess-Martin periodinane / CH₂Cl₂ / 0 °C

19.1: toluene / -78 °C

20.1: HCl / tetrahydrofuran; H₂O / 60 °C

21.1: NaBH₄ / methanol / 0 °C

22.1: n-Bu₃P / tetrahydrofuran / 20 °C

23.1: H₂O₂; NaHCO₃ / tetrahydrofuran; H₂O / 40 °C

24.1: 66 percent / n-Bu₄N⁽¹⁺⁾*I^(1-) / tetrahydrofuran; dimethylformamide / Heating

25.1: tetrahydrofuran / 0 °C

25.2: n-BuLi / tetrahydrofuran; diethyl ether / -78 - -40 °C

26.1: H₂; Lindlar catalyst; quinoline / ethyl acetate / 20 °C

With quinoline; hydrogenchloride; dmap; sodium tetrahydroborate; Lindlar's catalyst; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; tributylphosphine; thexyl borane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); triethylamine; lithium chloride; copper(I) bromide; lithium bromide; ruthenium; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; 2.1: Swern oxidation;
DOI:10.1002/anie.200501925