(1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane

Base Information

• Chemical Name: (1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane
• CAS No.: 853750-28-4
• Molecular Formula: C₅₉H₇₄O₈Si₃
• Molecular Weight: 995.488
• Mol file: 853750-28-4.mol

Synonyms:(1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane

Chemical Property of (1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane

There total 10 articles about (1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane 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: 20.0%

(2S,3S,4R)-1-Benzo[1,3]dioxol-5-yl-2,3-bis-(tert-butyl-diphenyl-silanyloxymethyl)-4-(3,4-dimethoxy-phenyl)-4-triethylsilanyloxy-butan-1-ol → (1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane (853750-28-4)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1039/b501151e

Reference yield:

(3S,4R)-4-(3,4-Dimethoxy-phenyl)-3-hydroxymethyl-4-triethylsilanyloxy-butyraldehyde → (1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane (853750-28-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 3.77 g / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h / 20 °C

2.1: KHMDS / tetrahydrofuran; toluene / 0.25 h / -70 °C

2.2: tetrahydrofuran; toluene / 1 h / -70 °C

3.1: LiBH₄ / tetrahydrofuran / 16 h / 0 °C

4.1: 7.02 g / Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

5.1: 20 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 48 h / 20 °C

With dmap; lithium borohydride; 4 A molecular sieve; potassium hexamethylsilazane; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/b501151e

Reference yield:

(S)-3-[(R)-(3,4-dimethoxyphenyl)(triethylsilyloxy)methyl]-4-butanolide (853750-40-0) → (1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane (853750-28-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: KHMDS / tetrahydrofuran; toluene / 0.25 h / -70 °C

1.2: tetrahydrofuran; toluene / 1 h / -70 °C

2.1: LiBH₄ / tetrahydrofuran / 16 h / 0 °C

3.1: 7.02 g / Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

4.1: 20 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 48 h / 20 °C

With dmap; lithium borohydride; 4 A molecular sieve; potassium hexamethylsilazane; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/b501151e

upstream raw materials:

(S)-3-[(R)-(3,4-dimethoxyphenyl)(triethylsilyloxy)methyl]-4-butanolide

(S)-2-[(R)-(3,4-dimethoxyphenyl)(triethylsilyloxy)methyl]-4-penten-1-ol

(4R)-4-benzyl-3-{(2R)-2-[(R)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone

(R)-4-benzyl-3-{(R)-2-[(R)-(3,4-dimethoxyphenyl)(triethylsilyloxy)-methyl]-4-pentenoyl}-2-oxazolidinone