(2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal

Base Information

• Chemical Name: (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal
• CAS No.: 187862-57-3
• Molecular Formula: C₃₃H₄₄O₃Si
• Molecular Weight: 516.796
• Mol file: 187862-57-3.mol

Synonyms:(2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal

Chemical Property of (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal

There total 18 articles about (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal 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: 89.0%

(E)-(5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undec-3-enoic acid methyl ester (187862-52-8) → (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal (187862-57-3)

Guidance literature:

With dimethylsulfide; ozone; -78 deg C -> RT;

DOI:10.1016/S0040-4039(97)00096-8

Reference yield:

(R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-hexanal (187862-43-7) → (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal (187862-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 89 percent / TMSOTf / CH₂Cl₂ / 37 h / -78 - -55 °C

2.1: O₃ / pyridine / methanol / -78 °C

2.2: 89 percent / Me₂S / methanol / 12 h / -78 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; ozone; pyridine; In methanol; dichloromethane;

DOI:10.1021/jo001767c

Reference yield:

2-ethyl-1,3-propandiol (2612-29-5) → (2R,3S,6R)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-octanal (187862-57-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-BuLi / tetrahydrofuran; various solvent(s) / 1 h / -78 °C

1.2: 100 percent / tetrahydrofuran; various solvent(s) / 1 h / -30 °C

2.1: 48 percent / Lipase PS₃O / pentane / 24 h / 20 °C

3.1: 90 percent / K₂CO₃ / methanol / 13 h / 20 °C

4.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: LiN(Me₃Si)2 / tetrahydrofuran / 0.33 h / -10 - 20 °C

5.2: 7.63 g / tetrahydrofuran / 0.5 h / 0 °C

6.1: 83 percent / aq. HF / acetonitrile; CH₂Cl₂ / 2 h / 20 °C

7.1: 85 percent / imidazole / dimethylformamide / 14 h / -5 - 20 °C

8.1: H₂ / Pd/C; TFA / ethanol / 12 h / 760.05 Torr

9.1: 71 percent / DIBAL-H / tetrahydrofuran / 6.75 h / -78 - -50 °C

10.1: 90 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 25 °C

11.1: 89 percent / TMSOTf / CH₂Cl₂ / 37 h / -78 - -55 °C

12.1: O₃ / pyridine / methanol / -78 °C

12.2: 89 percent / Me₂S / methanol / 12 h / -78 - 20 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; Lipase PS₃O; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; ozone; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; pyridine; palladium on activated charcoal; trifluoroacetic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane;

DOI:10.1021/jo001767c

upstream raw materials:

(E)-(5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-undec-3-enoic acid methyl ester

(E)-(R)-4-Hydroxymethyl-hex-2-enoic acid methyl ester

(R)-2-((tert-butyldimethylsilyloxy)methyl)butan-1-ol

(2-acetoxymethylbutoxy)-tert-butyldimethylsilane

Downstream raw materials:

(E)-(5S,6S,7S,8S,11R)-8-Benzyloxy-11-(tert-butyl-diphenyl-silanyloxymethyl)-6-hydroxy-4,5,7-trimethyl-tridec-3-enoic acid methyl ester

(4S,5S,6S,9R)-6-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-2,5-dimethyl-undec-1-en-4-ol

rutamycin B

C₄₃H₆₆O₃Si₂