(1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde

Base Information

Chemical Name:(1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde
CAS No.:1314123-79-9
Molecular Formula:C₄₁H₅₈O₄Si₂
Molecular Weight:671.08
Hs Code.:

Synonyms:(1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde

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Chemical Property of (1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde

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Technology Process of (1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde

There total 1 articles about (1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde 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%

: (2S,5S)-2-(3-(benzyloxy)propyl)-4-((tert-butyldiphenylsilyloxy)methyl)-1-hydroxy-5-methylcyclohex-3-enecarbaldehyde

: 69739-34-0
t-butyldimethylsiyl triflate

: 1314123-79-9
(1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 0.666667h; Inert atmosphere;
DOI:10.1002/anie.201102037

Reference yield: 60.0%

: 1314123-77-7
(5S,6R,8S)-ethyl 5-hydroxy-6,8-dimethyl-3-oxodec-9-enoate

: 1314123-79-9
(1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde

: 1314123-80-2
(2R,6S)-ethyl 2-((1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enyl)-6-((2R,4S)-4-methylhex-5-en-2-yl)-4-oxotetrahydro-2H-pyran-3-carboxylate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - -40 ℃; for 0.75h; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201102037

Reference yield:

: 1314123-79-9
(1S,2S,5S)-2-(3-(benzyloxy)propyl)-1-(tert-butyldimethylsilyloxy)-4-((tertbutyldiphenylsilyloxy)methyl)-5-methylcyclohex-3-enecarbaldehyde

: 1314123-82-4
(1S,2S,2'S,4a'R,5S,7a'R)-2-allyl-4-((tert-butyldiphenylsilyloxy)methyl)-4a',5-dimethyl-2'-((2R,4S)-4-methylhex-5-en-2-yl)-2',3'-dihydrospiro[cyclohex[3]ene-1,7'-furo[3,4-b]pyran]-4',5'(4a'H,7a'H)-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.75 h / -78 - -40 °C / Inert atmosphere

2.1: hydrogen fluoride; water / acetonitrile / 18 h / 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / Inert atmosphere

3.2: Inert atmosphere

4.1: potassium carbonate / acetonitrile / 2 h / 70 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

6.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 22 h / Inert atmosphere

7.1: tributylphosphine / tetrahydrofuran / 1 h / Inert atmosphere

8.1: dihydrogen peroxide / tetrahydrofuran; water / 18 h / 0 °C / Inert atmosphere

With 1H-imidazole; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; hydrogen fluoride; potassium tert-butylate; water; dihydrogen peroxide; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1002/anie.201102037