(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

Base Information

• Chemical Name: (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid
• CAS No.: 135383-56-1
• Molecular Formula: C₁₈H₂₇NO₅
• Molecular Weight: 337.416
• Mol file: 135383-56-1.mol

Synonyms:(3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

Chemical Property of (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid

There total 6 articles about (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid 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: 99.0%

tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate (120205-58-5) → (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid (135383-56-1)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1039/p19960000853

Reference yield: 97.0%

[(1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-((4R,5S)-4-methyl-2-oxo-5-phenyl-oxazolidin-3-yl)-4-oxo-butyl]-methyl-carbamic acid benzyl ester → (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid (135383-56-1)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 3h;

DOI:10.1039/p19960000853

Reference yield:

N-Cbz-L-Isoleucine (3160-59-6) → (3R,4S,5S)-4--3-methoxy-5-methylheptanoic acid (135383-56-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) CDI / 1) THF

2: 90 percent / NaBH₄ / methanol

3: 1) lithium hexamethyldisilazide (LHMDS) / 1) THF, HMPA, -78 deg C, 25 min, 2) -20 deg C, 15 min

4: HCOOH

With sodium tetrahydroborate; formic acid; 1,1'-carbonyldiimidazole; lithium hexamethyldisilazane; In methanol;

DOI:10.1016/S0040-4039(00)79932-1

upstream raw materials:

tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate

(3R,4S,5S)-4-(Benzyloxycarbonyl-methyl-amino)-3-methoxy-5-methyl-heptanoic acid methyl ester

N-Cbz-L-Isoleucine

(3R,4S,5S)-4-Benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid tert-butyl ester

Downstream raw materials:

Cbz-Dil-Dap-Doe

tert-Butyl (3R,4S,5S)-3-methoxy-4--5-methylheptanoate

(S)-N-{(S)-1-[((1S,2R)-1-((S)-sec-Butyl)-2-methoxy-4-{(S)-2-[(1R,2S)-1-methoxy-2-((S)-2-phenyl-1-thiazol-2-yl-ethylcarbamoyl)-propyl]-pyrrolidin-1-yl}-4-oxo-butyl)-methyl-carbamoyl]-2-methyl-propyl}-2-dimethylamino-3-methyl-butyramide

dolastatin 10