(2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate

Base Information

• Chemical Name: (2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate
• CAS No.: 123487-23-0
• Molecular Formula: C₃₀H₄₄O₅Si
• Molecular Weight: 512.762
• Mol file: 123487-23-0.mol

Synonyms:(2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate

Chemical Property of (2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate

There total 19 articles about (2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate 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: 78.0%

(2R,3R,8R)-methyl 2-(hydroxymethyl)-3-hydroxy-8-methyl-10-oxoundecanoate (146500-59-6) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate (123487-23-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 3h;

DOI:10.1021/jo00058a057

Reference yield: 72.0%

(2R,3R,8R)-methyl 2-<((-tert-butyldiphenylsilyl)oxy)methyl>-3-<(2-methoxyethoxy)>-8-methyl-10-oxoundecanoate (123487-22-9) → (2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate (123487-23-0)

Guidance literature:

With zinc dibromide; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jo00285a017

Reference yield:

(6R)-6-methyl-8,8-(ethylenedioxy)nonanal (123487-17-2) → (2R,3R,8R)-methyl 2-<((tert-butyldiphenylsilyl)oxy)methyl>-3-hydroxy-8-methyl-10-oxoundecanoate (123487-23-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) lithium bis(trimethylsilyl)amide / 1) THF, -10 deg C, 45 min, 2) THF, -100 deg C, 1.25 h

2: 90 percent / potassium carbonate / 3 h / Ambient temperature

3: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1.0 h, 2a) -78 deg C up to -25 deg C, 4.0 h, 2b) -25 deg C, 12.0 h

4: 100 percent / hydrogen / 10percent Pd-C / ethyl acetate / 1 h / 2585.7 Torr

5: 78 percent / imidazole / dimethylformamide / 3 h

With 1H-imidazole; hydrogen; potassium carbonate; lithium hexamethyldisilazane; lithium diisopropyl amide; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00058a057

upstream raw materials:

(2R,3R,8R)-methyl 2-<((-tert-butyldiphenylsilyl)oxy)methyl>-3-<(2-methoxyethoxy)>-8-methyl-10-oxoundecanoate

(2R,3R,8R)-methyl 2-(hydroxymethyl)-3-hydroxy-8-methyl-10-oxoundecanoate

tert-butylchlorodiphenylsilane

(6R)-6-methyl-8,8-(ethylenedioxy)nonanal

Downstream raw materials:

(2'R,3'R,5RS,7R)-tert-butyl 11-<3'-(((tert-butyldiphenylsilyl)oxy)methyl)-4'-oxo-2'-oxetanyl>-5-hydroxy-3,5,7-trimethyl-2-undecenoate

(2'R,3'R,7R)-(E,E)-tert-butyl 11-<3'-(((tert-butyldiphenylsilyl)oxy)methyl)-4'-oxo-2'-oxetanyl>-3,5,7-trimethyl-2,4-undecadienoate

6-{(R)-6-[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-oxo-oxetan-2-yl]-2-methyl-hexyl}-4,6-dimethyl-5,6-dihydro-pyran-2-one

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