(S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate

Base Information

• Chemical Name: (S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate
• CAS No.: 854022-23-4
• Molecular Formula: C₂₁H₃₅NO₅Si
• Molecular Weight: 409.598
• Mol file: 854022-23-4.mol

Synonyms:(S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate

Chemical Property of (S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate

There total 12 articles about (S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate 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:

{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-1-formyl-ethyl}-carbamic acid allyl ester (854022-39-2) → (S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate (854022-23-4)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;

DOI:10.1021/jo8021988

Reference yield:

2-(benzhydrylidene-amino)-3-[4-methoxy-3-methyl-5-(toluene-4-sulfonyloxy)-phenyl]-propionic acid tert-butyl ester → (S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate (854022-23-4)

Guidance literature:

Multi-step reaction with 6 steps

1: AcOH / tetrahydrofuran; H₂O / 2 h / 20 °C

2: LiBH₄ / diethyl ether; methanol / 20 °C

3: NaOH / ethanol; H₂O / 8 h / 80 °C

4: NaHCO₃ / H₂O; CH₂Cl₂ / 1 h / 20 °C

5: imidazole / dimethylformamide / 2 h / 20 °C

6: aq.HCl / H₂O; tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; lithium borohydride; sodium hydrogencarbonate; acetic acid; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo050408k

Reference yield:

3-methylbenzene-1,2-diol (488-17-5) → (S)-allyl 1-hydroxy-3-(3-tert-butyldimethylsilyloxy-4-methoxy-5-methylphenyl)propan-2-ylcarbamate (854022-23-4)

Guidance literature:

Multi-step reaction with 12 steps

1: triethylamine / CH₂Cl₂ / 4 h / -70 °C

2: 23.5 g / K₂CO₃ / acetone / 5 h / 50 °C

3: 85 percent / TiCl₄ / CH₂Cl₂ / 20 °C

4: 99 percent / NaBH₄ / tetrahydrofuran; methanol; H₂O / 1 h / 0 °C

5: 95 percent / PBr₃ / CH₂Cl₂; toluene / 20 °C

6: O-⁽⁹⁾-allyl-N-(9'-anthracenylmethyl)cinchonidium bromide; CsOH*H₂O / CH₂Cl₂ / 30 h / -78 °C

7: AcOH / tetrahydrofuran; H₂O / 2 h / 20 °C

8: LiBH₄ / diethyl ether; methanol / 20 °C

9: NaOH / ethanol; H₂O / 8 h / 80 °C

10: NaHCO₃ / H₂O; CH₂Cl₂ / 1 h / 20 °C

11: imidazole / dimethylformamide / 2 h / 20 °C

12: aq.HCl / H₂O; tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; cesium hydroxide; sodium hydroxide; sodium tetrahydroborate; lithium borohydride; phosphorus tribromide; titanium tetrachloride; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo050408k

upstream raw materials:

3-methylbenzene-1,2-diol

toluene-4-sulfonic acid 2-hydroxy-3-methyl-phenyl ester

toluene-4-sulfonic acid 2-methoxy-3-methyl-phenyl ester

(S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol

Downstream raw materials:

{2-(11-allyloxy-7-hydroxymethyl-2,2,12-trimethyl-4,5,7,10-tetrahydro-1,3,15,17-tetraoxa-6-aza-cyclopenta[a]phenanthren-6-yl)-1-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-benzyl]-2-cyano-ethyl}-carbamic acid allyl ester

C₆₉H₈₃Cl₃N₄O₁₆SSi

{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-1-formyl-ethyl}-carbamic acid allyl ester