(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

Base Information

• Chemical Name: (2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol
• CAS No.: 870135-88-9
• Molecular Formula: C₂₇H₃₈O₇
• Molecular Weight: 474.595

Synonyms:(2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

Chemical Property of (2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

There total 22 articles about (2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-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:

(2S,3S,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol (870135-80-1) → (2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol (870135-88-9)

Guidance literature:

Multi-step reaction with 15 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

With dmap; n-butyllithium; ammonium cerium(IV) nitrate; tributylphosphine; thexyl borane; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 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 → (2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol (870135-88-9)

Guidance literature:

Multi-step reaction with 19 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

With dmap; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; tributylphosphine; thexyl borane; tetrabutyl ammonium fluoride; dihydrogen peroxide; 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; dichloromethane; water; toluene; acetonitrile; 2.1: Swern oxidation;

DOI:10.1002/anie.200501925

Reference yield:

(4aR,6S,8S,8aR)-6-Allyl-8-benzyloxy-2,2-di-tert-butyl-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-7-one → (2R,3S,4aR,5aS,6aR,8S,10aS,11aS,12S,12aR)-2-Allyl-12-benzyloxy-8-methoxy-3,11a-dimethyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol (870135-88-9)

Guidance literature:

Multi-step reaction with 17 steps

1.1: toluene / -78 °C

2.1: 98 percent / (HF)3*NEt₃ / tetrahydrofuran / 0 °C

3.2: 88 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

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

4.2: 78 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 °C

5.1: KH / tetrahydrofuran

5.2: 88 percent / n-BuLi / diethyl ether / -78 - -40 °C

6.1: 85 percent / CuBr; LiBr / tetrahydrofuran / -95 - -78 °C

7.1: 84 percent / CuCn; LiCl / tetrahydrofuran / -78 °C

8.1: 89 percent / ruthenium complex / toluene / 70 °C

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

9.2: 62 percent / NaBO₃*4H₂O; pH 7 buffer / tetrahydrofuran

10.1: 71 percent / TsOH / 20 °C

11.1: DMAP; Et₃N / CH₂Cl₂ / 20 °C

12.1: CAN / acetonitrile; H₂O / 20 °C

13.1: nBu₃P / tetrahydrofuran / 20 °C

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

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

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

17.1: toluene / -78 °C

With dmap; n-butyllithium; ammonium cerium(IV) nitrate; tributylphosphine; thexyl borane; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine tris(hydrogen fluoride); triethylamine; lithium chloride; copper(I) bromide; lithium bromide; ruthenium; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;

DOI:10.1002/anie.200501925

upstream raw materials:

methyl magnesium iodide

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

(2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol

(2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3,5-bis-ethynyloxy-3-methyl-tetrahydro-pyran

Downstream raw materials:

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

(2R,3S,4aR,6R,7S,8aS,9S,9aR,10aS)-2-Allyl-9-benzyloxy-7-(3-hydroxy-propyl)-3,8a-dimethyl-decahydro-1,8,10-trioxa-anthracene-3,6-diol

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

(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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