(2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

Base Information

Chemical Name:(2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol
CAS No.:476688-29-6
Molecular Formula:C₃₄H₄₆O₁₀
Molecular Weight:614.733
Hs Code.:

(2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

Synonyms:(2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

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Chemical Property of (2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

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Technology Process of (2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

There total 20 articles about (2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-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: 91.0%

: 476688-27-4
1-[5-benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-4-[3,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-tetrahydro-pyran-2-yl]-butane-2,3-dione

: 149-73-5
trimethyl orthoformate

: 476688-29-6
(2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

Guidance literature:: With camphor-10-sulfonic acid; In methanol; at 80 ℃;
DOI:10.1021/ol026804w

Reference yield:

: 476688-30-9
(4aR,6S,7R,8aS)-6-(2-Hydroxy-ethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 476688-29-6
(2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / NaH; n-Bu₄NI / tetrahydrofuran / 20 °C

2.1: 95 percent / CSA / methanol / 20 °C

3.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

3.2: 73 percent / CH₂Cl₂ / -78 °C

4.1: 75 percent / t-BuLi; HMPA / tetrahydrofuran / -78 °C

5.1: CSA / methanol / 20 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

7.1: 73 percent / NaIO₄ / RuO₂ / acetonitrile; CCl₄; H₂O / 20 °C

8.1: 91 percent / CSA / methanol / 80 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; camphor-10-sulfonic acid; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; ruthenium(IV) oxide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1021/ol026804w

Reference yield:

: (2R,3S,5R,6S)-6-{4-[(2R,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-ynyl}-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxymethyl-2-methyl-tetrahydro-pyran-3-ol

: 476688-29-6
(2R,3S,4aR,5aS,6aR,8S,9R,10aS,11aR,12aS)-9-Benzyloxy-8-(2-benzyloxy-ethyl)-2-hydroxymethyl-5a,11a-dimethoxy-2-methyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 73 percent / NaIO₄ / RuO₂ / acetonitrile; CCl₄; H₂O / 20 °C

3: 91 percent / CSA / methanol / 80 °C

With 2,6-dimethylpyridine; sodium periodate; camphor-10-sulfonic acid; ruthenium(IV) oxide; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1021/ol026804w