(4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester
• CAS No.: 185810-88-2
• Molecular Formula: C₁₅H₂₆O₅Si
• Molecular Weight: 314.454
• Mol file: 185810-88-2.mol

Synonyms:(4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

Chemical Property of (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

There total 12 articles about (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester 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: 90.0%

t-butyldimethylsiyl triflate (69739-34-0) + (4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester (185810-87-1) → (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester (185810-88-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1021/jo961713w

Reference yield:

D-(-)-quinic acid (77-95-2) → (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester (185810-88-2)

Guidance literature:

Multi-step reaction with 7 steps

1: p-TsOH*H₂O / dimethylformamide; benzene / 12 h / Heating

2: 1.) Bu₂SnO / 1.) DMF, benzene, reflux, 4h, 2.) DMF, benzene, reflux, 6 h

3: 90 percent / KH / tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h

4: 98 percent / H₂ / Pd(OH)2/C / methanol / Ambient temperature

5: 90 percent / NaIO₄, RuO₂*xH₂O / ethyl acetate; H₂O; acetone / 16 h / Ambient temperature

6: 90 percent / KHCO₃ / methanol / 12 h / Ambient temperature

7: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

With 2,6-dimethylpyridine; ruthenium(IV) oxide; sodium periodate; hydrogen; potassium hydride; di(n-butyl)tin oxide; potassium hydrogencarbonate; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo961713w

Reference yield:

(1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone (185810-83-7) → (4S,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester (185810-88-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / KH / tetrahydrofuran / 1.) room temperature, 1 h, 2.) reflux, 1 h

2: 98 percent / H₂ / Pd(OH)2/C / methanol / Ambient temperature

3: 90 percent / NaIO₄, RuO₂*xH₂O / ethyl acetate; H₂O; acetone / 16 h / Ambient temperature

4: 90 percent / KHCO₃ / methanol / 12 h / Ambient temperature

5: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

With 2,6-dimethylpyridine; ruthenium(IV) oxide; sodium periodate; hydrogen; potassium hydride; potassium hydrogencarbonate; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1021/jo961713w

upstream raw materials:

t-butyldimethylsiyl triflate

(4S,5R)-5-hydroxy-4-methoxy-3-oxocyclohex-1-ene-1-carboxylic acid methyl ester

(3R,4S,5R)-3,5-bis{[(tert-butyl)dimethylsilyl]oxy}-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

(3R,4S,5R)-3,5-dihydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

Downstream raw materials:

(3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(2-iodo-acetoxy)-4-methoxy-3-vinyl-cyclohex-1-enecarboxylic acid methyl ester

(3S,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(2-chloro-acetoxy)-4-methoxy-3-vinyl-cyclohex-1-enecarboxylic acid methyl ester

(3S,4R,5R)-3-[(1RS)-2-bromo-1-ethoxyethoxy]-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester

(3S,4R,5R)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-4-methoxycyclohex-1-ene-1-carboxylic acid methyl ester