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

Base Information

• Chemical Name: (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (1S,5R,6S)-6-benzyloxy-5-methoxy-cyclohex-2-enyl ester
• CAS No.: 135708-84-8
• Molecular Formula: C₄₃H₇₀O₇Si₂
• Molecular Weight: 755.196
• Mol file: 135708-84-8.mol

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

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

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 (1S,5R,6S)-6-benzyloxy-5-methoxy-cyclohex-2-enyl ester

There total 18 articles about (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (1S,5R,6S)-6-benzyloxy-5-methoxy-cyclohex-2-enyl ester 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: 75.0%

(1S,5R,6R)-6-Benzyloxy-5-methoxy-cyclohex-2-enol (135708-74-6) + (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (135708-83-7) → (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (1S,5R,6S)-6-benzyloxy-5-methoxy-cyclohex-2-enyl ester (135708-84-8)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/jo00020a026

Reference yield:

benzyl bromide (100-39-0) → (3R,4S,6S,7R)-8-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (1S,5R,6S)-6-benzyloxy-5-methoxy-cyclohex-2-enyl ester (135708-84-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH, 2) Bu₄NI / 1) DMF, 0 deg C, 15 min, 2) r.t., 21 h

2: 85 percent / HgCl₂ / acetone; H₂O / 2 h / Heating

3: 91 percent / MsCl, pyridine / 12 h / Ambient temperature

4: 1) CeCl₃*7H₂O, 2) LiBH₄ / 1) THF, MeOH, 2) -78 deg C, 0.5 h

5: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; dmap; lithium borohydride; cerium(III) chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; methanesulfonyl chloride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; mercury dichloride; In dichloromethane; water; acetone;

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 (1S,5R,6S)-6-benzyloxy-5-methoxy-cyclohex-2-enyl ester (135708-84-8)

Guidance literature:

Multi-step reaction with 9 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

9: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; 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; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00020a026

upstream raw materials:

(1S,5R,6R)-6-Benzyloxy-5-methoxy-cyclohex-2-enol

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

benzyl bromide

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

Downstream raw materials:

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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

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