3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol

Base Information

Chemical Name:3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol
CAS No.:870135-86-7
Molecular Formula:C₃₂H₅₂O₈Si
Molecular Weight:592.846
Hs Code.:

3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol

Synonyms:3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol

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Chemical Property of 3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol

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Technology Process of 3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol

There total 17 articles about 3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-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:

: [(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-8-methoxy-11a-methyl-2-(3-pentamethylphenyloxy-propyl)-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-yloxy]-tert-butyl-dimethyl-silane

: 870135-86-7
3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; 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

: 870135-86-7
3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 10 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

With dmap; n-butyllithium; ammonium cerium(IV) nitrate; thexyl borane; potassium hydride; toluene-4-sulfonic acid; triethylamine; lithium chloride; copper(I) bromide; lithium bromide; ruthenium; In tetrahydrofuran; dichloromethane; water; 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

: 870135-86-7
3-[(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-12-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11a-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 14 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

With dmap; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; thexyl borane; potassium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); triethylamine; lithium chloride; copper(I) bromide; lithium bromide; ruthenium; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; 2.1: Swern oxidation;
DOI:10.1002/anie.200501925