(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Base Information

• Chemical Name: (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester
• CAS No.: 185201-24-5
• Molecular Formula: C₅₁H₈₂O₁₃Si
• Molecular Weight: 931.29
• Mol file: 185201-24-5.mol

Synonyms:(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Chemical Property of (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

There total 11 articles about (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl 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: 91.0%

(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-[(4S,5R)-4-(4-methoxy-benzyloxymethoxy)-5-methyl-3-methylene-6-phenyl-hexyl]-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (185201-23-4) → (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (185201-24-5)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 2.5h; Ambient temperature;

DOI:10.1021/jo961533m

Reference yield:

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester (144358-24-7) → (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (185201-24-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / imidazole / dimethylformamide / 28 h / Ambient temperature

2: 98 percent / CeCl₃, EtMgCl / tetrahydrofuran / 0.25 h / -78 °C

3: 96 percent / i-Pr₂NEt / CH₂Cl₂ / Ambient temperature

4: 91 percent / DDQ, H₂O / CH₂Cl₂ / 2.5 h / Ambient temperature

With 1H-imidazole; cerium(III) chloride; water; ethylmagnesium chloride; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo961533m

Reference yield:

[1S-(1α(4S,5R),3α,4β,5α,6α,7β)]-1-(4-acetyloxy-5-methyl-3-methylene-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,4,5-tris(1,1-dimethylethyl) ester (171336-39-3) → (1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-((4S,5R)-4-hydroxy-5-methyl-3-methylene-6-phenyl-hexyl)-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester (185201-24-5)

Guidance literature:

Multi-step reaction with 5 steps

1: DMAP, DCC / CH₂Cl₂ / 12 h / Ambient temperature

2: 93 percent / imidazole / dimethylformamide / 28 h / Ambient temperature

3: 98 percent / CeCl₃, EtMgCl / tetrahydrofuran / 0.25 h / -78 °C

4: 96 percent / i-Pr₂NEt / CH₂Cl₂ / Ambient temperature

5: 91 percent / DDQ, H₂O / CH₂Cl₂ / 2.5 h / Ambient temperature

With 1H-imidazole; dmap; cerium(III) chloride; water; ethylmagnesium chloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo961533m

upstream raw materials:

(1S,3S,4S,5R,6R,7R)-6-((E)-(4S,6S)-4,6-Dimethyl-oct-2-enoyloxy)-4-hydroxy-1-[(4S,5R)-4-(4-methoxy-benzyloxymethoxy)-5-methyl-3-methylene-6-phenyl-hexyl]-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

triethylsilyl chloride

2-tert-butyl-1,3-diisopropylisourea

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester

Downstream raw materials:

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-4-Acetoxy-5-methyl-3-methylene-6-phenyl-hexyl)-6-((E)-(4S,6S)-4,6-dimethyl-oct-2-enoyloxy)-4-hydroxy-7-triethylsilanyloxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester

<1S-<1α(4R*,5R*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 3,4,5-tris(1,1-dimethylethyl) ester

zaragozic acid A

(1S,3S,4S,5R,6R,7R)-1-((4S,5R)-3,4-Dihydroxy-5-methyl-6-phenyl-hexyl)-4,6,7-trihydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid tri-tert-butyl ester