(1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane
• CAS No.: 528865-19-2
• Molecular Formula: C₄₇H₅₆O₁₀
• Molecular Weight: 780.956
• Mol file: 528865-19-2.mol

Synonyms:(1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

Chemical Property of (1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

There total 1 articles about (1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane 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: 78.0%

Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester (528865-17-0) → (1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane (528865-19-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(02)01514-4

Reference yield: 98.0%

benzoyl chloride (98-88-4) + (1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane (528865-19-2) → (1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-6,7-bisbenzoyloxy-3,4,5-tris-benzyloxymethyl-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:

With pyridine; dmap; at 20 ℃; for 30h;

DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

(1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-3,4,5-tris-benzyloxymethyl-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane (528865-19-2) → (1S,3R,4S,5R,6R,7R,4'R,5'R,7'E)-1-[4'-acetoxy-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-6,7-bisbenzoyloxy-4-hydroxy-3,4,5-trihydroxymethyl-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / DMAP; pyridine / 30 h / 20 °C

2: 65 percent / BCl₃*SMe₂ / CH₂Cl₂ / 21 h / 20 °C

With pyridine; dmap; boron trichloride - methyl sulfide complex; In dichloromethane;

DOI:10.1016/S0040-4020(02)01514-4

upstream raw materials:

Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester