(3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid

Base Information

• Chemical Name: (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid
• CAS No.: 135708-83-7
• Molecular Formula: C₂₉H₅₄O₅Si₂
• Molecular Weight: 538.916
• Mol file: 135708-83-7.mol

Synonyms:(3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid

Chemical Property of (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid

There total 9 articles about (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic 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%

(3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanal (135708-82-6) → (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (135708-83-7)

Guidance literature:

With potassium permanganate; sodium dihydrogenphosphate; In water; tert-butyl alcohol;

DOI:10.1021/jo00020a026

Reference yield:

(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene (89046-67-3,91796-47-3,91796-48-4,91798-02-6,91798-03-7,94233-73-5,94233-74-6,106357-32-8) → (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (135708-83-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

2: 1) O₃, pyridine, 2) DMS / 1) MeOH, CH₂Cl₂, -78 deg C, 2) r.t., 15 h

3: 2) 15percent aq.NaOH / 1) toluene, -78 deg C, 2 h, 2) r.t., 16 h

4: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

6: 1) 9-BBN, 2) 30percent H₂O₂, 3M NaOH / 1) THF, r.t., 4 h, 2) 0 deg C, 1 h

7: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

8: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

With pyridine; 1H-imidazole; sodium hydroxide; potassium permanganate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 2,3-dimercapto-succinic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00020a026

Reference yield:

[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane (135708-75-7,135708-76-8) → (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (135708-83-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) O₃, pyridine, 2) DMS / 1) MeOH, CH₂Cl₂, -78 deg C, 2) r.t., 15 h

2: 2) 15percent aq.NaOH / 1) toluene, -78 deg C, 2 h, 2) r.t., 16 h

3: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

5: 1) 9-BBN, 2) 30percent H₂O₂, 3M NaOH / 1) THF, r.t., 4 h, 2) 0 deg C, 1 h

6: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

7: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

With pyridine; 1H-imidazole; sodium hydroxide; potassium permanganate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 2,3-dimercapto-succinic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00020a026

upstream raw materials:

(3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanal

(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene

[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane

(R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanal

Downstream raw materials:

(3R,4S,6S,7R)-8-Benzyloxy-2-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

C₄₉H₈₄O₇Si₃

C₄₉H₈₄O₇Si₃

(3R,4S,6S,7R)-8-Benzyloxy-2-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid