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

Base Information

• Chemical Name: 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
• CAS No.: 128684-73-1
• Molecular Formula: C₃₁H₅₂O₆Si
• Molecular Weight: 548.836
• Mol file: 128684-73-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 70.0%

2-Benzenesulfonyl-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 (128684-72-0) → 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 (128684-73-1)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at 0 ℃; for 3h;

DOI:10.1021/ja00170a024

Reference yield:

(1R,2R,4R)-4-(iodomethyl)-2-methoxycyclohexan-1-ol (118207-42-4) → 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 (128684-73-1)

Guidance literature:

Multi-step reaction with 5 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

With disodium hydrogenphosphate; sodium amalgam; n-butyllithium; Dess-Martin periodane; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00170a024

Reference yield:

(-)-(1R,2R,4R)-4-hydroxymethyl-2-methoxycyclohexan-1-ol (109466-73-1) → 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 (128684-73-1)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; iodine; Dess-Martin periodane; triethylamine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00170a024

upstream raw materials:

2-Benzenesulfonyl-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

(-)-(1R,2R,4R)-4-hydroxymethyl-2-methoxycyclohexan-1-ol

(1R,2R,4R)-4-(iodomethyl)-2-methoxycyclohexan-1-ol

(4R,5S)-5-ethenyl-4-methoxytetrahydro-2H-pyran-2-one

Downstream raw materials:

((1R,2R,4S)-4-{2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-allyl}-2-methoxy-cyclohexyloxy)-tert-butyl-dimethyl-silane

((1R,2R,4R)-4-{(E)-2-[(4S,5R,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-propenyl}-2-methoxy-cyclohexyloxy)-tert-butyl-dimethyl-silane

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