2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-ol

Base Information

Chemical Name:2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-ol
CAS No.:128684-74-2
Molecular Formula:C₃₂H₅₆O₆Si
Molecular Weight:564.879
Hs Code.:

Synonyms:2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-ol

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Chemical Property of 2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-ol

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Technology Process of 2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-ol

There total 13 articles about 2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-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: 76.0%

: 75-16-1
methylmagnesium bromide

: 128684-73-1
1-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-ethanone

: 128684-74-2
2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-ol

Guidance literature:: In tetrahydrofuran; toluene; at 0 ℃; for 0.166667h;
DOI:10.1021/ja00170a024

Reference yield:

: 118207-42-4
(1R,2R,4R)-4-(iodomethyl)-2-methoxycyclohexan-1-ol

: 128684-74-2
2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: dimethylformamide / 0.33 h / 100 °C

2: Et₃N / CH₂Cl₂ / Ambient temperature

3: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 2 h

4: 70 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

5: 70 percent / 6percent Na/Hg, Na₂HPO₄ / methanol / 3 h / 0 °C

6: 76 percent / tetrahydrofuran; toluene / 0.17 h / 0 °C

With disodium hydrogenphosphate; sodium amalgam; n-butyllithium; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja00170a024

Reference yield:

: 109466-73-1
(-)-(1R,2R,4R)-4-hydroxymethyl-2-methoxycyclohexan-1-ol

: 128684-74-2
2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-propan-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / I₂, PPh₃, pyridine / benzene / 2 h / Heating

2: dimethylformamide / 0.33 h / 100 °C

3: Et₃N / CH₂Cl₂ / Ambient temperature

4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 2 h

5: 70 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

6: 70 percent / 6percent Na/Hg, Na₂HPO₄ / methanol / 3 h / 0 °C

7: 76 percent / tetrahydrofuran; toluene / 0.17 h / 0 °C

With pyridine; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; iodine; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja00170a024