(2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-ol

Base Information

Chemical Name:(2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-ol
CAS No.:144534-95-2
Molecular Formula:C₄₃H₇₂O₇Si
Molecular Weight:729.126
Hs Code.:

(2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-ol

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Chemical Property of (2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-ol

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Technology Process of (2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-ol

There total 2 articles about (2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-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:

: 152934-39-9
(2S)-2-<(4S,5S)-5-Ethyl-2,2-dimethyl-1,2-dioxan-4-yl>propan-1-ol

: 144534-95-2
(2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-ol

Guidance literature:: Multi-step reaction with 2 steps

2: 1.) t-BuLi / 1.) ether, -78 deg C

With tert.-butyl lithium;
DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

: 144534-92-9
(4R,5S)-5-Ethyl-4-((R)-2-iodo-1-methyl-ethyl)-2,2-dimethyl-[1,3]dioxane

: 144534-80-5
(2S,3R,5R,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-2-(4-methoxy-benzyloxy)-3-methyl-octanal

: 144534-95-2
(2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-ol

Guidance literature:: With tert.-butyl lithium; Yield given. Multistep reaction; 1.) ether, -78 deg C;
DOI:10.1016/S0040-4039(00)61140-1

Reference yield:

: 144534-95-2
(2S,5S,6R,8R,9S)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-8-ethyl-2-((4S,5S)-5-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-5-(4-methoxy-benzyloxy)-6-methyl-undecan-4-ol

: 144535-01-3,144606-49-5
(1R,2R,4R,5S)-5-Benzyloxy-4-ethyl-1-[(2S,4S,5S)-5-((S)-1-ethyl-2-hydroxy-butyl)-2,4-dimethyl-tetrahydro-furan-2-yl]-2-methyl-heptane-1,4-diol

Guidance literature:: Multi-step reaction with 14 steps

1: Swern oxidation

2: diethyl ether / -78 to -20 deg C

3: DDQ / CH₂Cl₂; H₂O / Ambient temperature

4: LiAlH₄ / diethyl ether / 0 °C

5: pyridine / 0 °C

6: 1N H₂SO₄ / tetrahydrofuran / Ambient temperature

7: K₂CO₃ / methanol / Ambient temperature

8: CSA / CH₂Cl₂ / 0 °C

9: imidazole / CH₂Cl₂ / 0 deg C to room temp.

10: TEA, DMAP / CH₂Cl₂ / Ambient temperature

11: 1N HCl / tetrahydrofuran / Ambient temperature

12: Swern oxidation

13: tetrahydrofuran / -78 to -20 deg C

14: n-Bu₄NF / dimethylformamide / Ambient temperature

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium aluminium tetrahydride; TEA; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)61140-1