(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid

Base Information

• Chemical Name: (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid
• CAS No.: 363610-69-9
• Molecular Formula: C₃₄H₆₂O₅Si
• Molecular Weight: 578.949

Synonyms:(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid

Chemical Property of (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid

There total 10 articles about (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic 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:

(2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanal → (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid (363610-69-9)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 20 ℃;

DOI:10.1016/S0040-4039(01)00893-0

Reference yield:

(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-pentane-1,3-diol (364041-40-7) → (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid (363610-69-9)

Guidance literature:

Multi-step reaction with 9 steps

1: CSA / CH₂Cl₂

2: DIBAL-H / CH₂Cl₂ / -78 - 0 °C

3: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4: 40 percent / tetrahydrofuran / 0 - 20 °C

5: nBu₄NF / tetrahydrofuran

6: 2,6-lutidine / CH₂Cl₂ / 0 °C

7: CSA / methanol; CH₂Cl₂ / 0 °C

8: SO₃-Py; Et₂iPrN; DMSO / CH₂Cl₂ / 0 °C

9: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; N,N-diethyl-N-isopropylamine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)00893-0

Reference yield:

tert-Butyl-{(S)-2-[(4R,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propoxy}-diphenyl-silane → (2R,3R,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecanoic acid (363610-69-9)

Guidance literature:

Multi-step reaction with 8 steps

1: DIBAL-H / CH₂Cl₂ / -78 - 0 °C

2: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

3: 40 percent / tetrahydrofuran / 0 - 20 °C

4: nBu₄NF / tetrahydrofuran

5: 2,6-lutidine / CH₂Cl₂ / 0 °C

6: CSA / methanol; CH₂Cl₂ / 0 °C

7: SO₃-Py; Et₂iPrN; DMSO / CH₂Cl₂ / 0 °C

8: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; N,N-diethyl-N-isopropylamine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)00893-0

upstream raw materials:

(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-pentane-1,3-diol

(2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol

(2R,3S,4S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentan-1-one

(2S,3S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-octadecan-1-ol

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