(4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide

Base Information

• Chemical Name: (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide
• CAS No.: 909270-41-3
• Molecular Formula: C₃₅H₅₄O₃Si
• Molecular Weight: 550.897
• Mol file: 909270-41-3.mol

Synonyms:(4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide

Chemical Property of (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide

There total 3 articles about (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide 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: 88.0%

(R)-5-((R)-1-hydroxypentadecyl)-dihydrofuran-2(3H)-one (909270-40-2) + tert-butyldiphenylsilyl triflate (92886-86-7) → (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide (909270-41-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; toluene; at 20 ℃; for 72h;

DOI:10.1021/jo060970q

Reference yield:

(E)-ethyl nonadec-4-enoate (909270-38-8) → (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide (909270-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: AD-mix-β; methanesulfonamide / H2O; 2-methyl-propan-2-ol / 19 h / 0 °C

1.2: KOH / methanol / 2 h / 60 °C

1.3: 74 percent / p-TsOH*H₂O / CH₂Cl₂ / 1.5 h / 20 °C

2.1: 88 percent / 2,6-lutidine / CH₂Cl₂; toluene / 72 h / 20 °C

With 2,6-dimethylpyridine; methanesulfonamide; AD-mix-β; In dichloromethane; water; toluene; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo060970q

Reference yield:

heptadec-1-en-3-ol (131248-35-6) → (4R,5R)-5-t-butyldiphenylsilyloxy-4-nonadecanolide (909270-41-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 77 percent / propionic acid / 2 h / 135 - 140 °C

2.1: AD-mix-β; methanesulfonamide / H2O; 2-methyl-propan-2-ol / 19 h / 0 °C

2.2: KOH / methanol / 2 h / 60 °C

2.3: 74 percent / p-TsOH*H₂O / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 88 percent / 2,6-lutidine / CH₂Cl₂; toluene / 72 h / 20 °C

With 2,6-dimethylpyridine; methanesulfonamide; AD-mix-β; propionic acid; In dichloromethane; water; toluene; tert-butyl alcohol; 1.1: Claisen ortho ester rearrangement / 2.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo060970q

upstream raw materials:

(R)-5-((R)-1-hydroxypentadecyl)-dihydrofuran-2(3H)-one

tert-butyldiphenylsilyl triflate

(E)-ethyl nonadec-4-enoate

heptadec-1-en-3-ol

Downstream raw materials:

(2S,3S,6R,7R)-7-(t-butyldiphenylsilyloxy)-6-methoxymethyloxy-2,3-epoxy-henicosan-1-ol

(2E,6R,7R)-7-(t-butyldiphenylsilyloxy)-6-methoxymethyloxy-2-henicosen-1-ol

(2E,6R,7R)-methyl 7-(t-butyldiphenylsilyloxy)-6-methoxymethyloxy-2-henicosenate

(2E,6R,7R)-methyl 7-t-(butyldiphenylsilyloxy)-6-hydroxy-2-henicosenate