(1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde

Base Information

• Chemical Name: (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde
• CAS No.: 1163128-49-1
• Molecular Formula: C₂₁H₃₂O₄Si
• Molecular Weight: 376.568
• Mol file: 1163128-49-1.mol

Synonyms:(1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde

Chemical Property of (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde

There total 4 articles about (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde 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: 88.0%

(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran (916154-05-7) → (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde (1163128-49-1)

Guidance literature:

In diphenylether; at 210 ℃; for 2h;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde (1163128-49-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; water / methanol / 20 °C

1.2: 1 h / 35 °C

2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

2.2: 2 h / -78 - 0 °C

3.1: diphenylether / 2 h / 210 °C / Inert atmosphere

With water; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In methanol; diphenylether; dichloromethane; 3.1: |Claisen Rearrangement;

DOI:10.1021/acs.orglett.1c03723

Reference yield:

((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol (916154-04-6) → (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carbaldehyde (1163128-49-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

1.2: 2 h / -78 - 0 °C

2.1: diphenylether / 2 h / 210 °C / Inert atmosphere

With sodium hydrogencarbonate; Dess-Martin periodane; In diphenylether; dichloromethane; 2.1: |Claisen Rearrangement;

DOI:10.1021/acs.orglett.1c03723

upstream raw materials:

(2R,3R,4R)-4-(tert-butyldimethylsilyloxy)-3-(p-methoxybenzyloxy)-2-vinyl-2,3-dihydro-2H-pyran

((2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-3,4-dihydro-2H-pyran-2-yl)methanol

p-Anisaldehyde dimethyl acetal

tert-butyldimethylsilyl chloride

Downstream raw materials:

ethyl (1S,5R,6R)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-3-cyclohexene-1-carboxylate