(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde

Base Information

Chemical Name:(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde
CAS No.:339291-66-6
Molecular Formula:C₂₆H₄₂O₄Si
Molecular Weight:446.703
Hs Code.:

Synonyms:(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde

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Chemical Property of (1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde

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Technology Process of (1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde

There total 10 articles about (1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde 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: 93.0%

: 339291-65-5
[(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol

: 339291-66-6
(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/jo005683f

Reference yield:

: 2403-58-9
4-methoxybenzaldehyde diethylacetal

: 339291-66-6
(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: 26.5 g / dimethylformamide / 3 h / 50 °C / 10 - 15 Torr

2.1: 83 percent / DIBAL / CH₂Cl₂; cyclohexane / 5 h / -78 °C

3.1: DMSO; oxalyl chloride; Et₃N

4.1: 18-crown-6/acetonitrile complex; KHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 1.788 g / tetrahydrofuran / 1 h / -78 °C

5.1: 97 percent / DIBAL / hexane; CH₂Cl₂ / -78 - 20 °C

6.1: 73 percent / DMAP / dimethylformamide / 20 °C

7.1: 93 percent / Dess-Martin perioninane / CH₂Cl₂ / 4 h / 20 °C

With dmap; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; acetonitrile; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.1: Swern oxidation;
DOI:10.1021/jo005683f

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 339291-66-6
(1S,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentanecarbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 73 percent / DMAP / dimethylformamide / 20 °C

2: 93 percent / Dess-Martin perioninane / CH₂Cl₂ / 4 h / 20 °C

With dmap; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo005683f