(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

Base Information

Chemical Name:(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane
CAS No.:208338-43-6
Molecular Formula:C₅₉H₆₂O₁₂
Molecular Weight:963.134
Hs Code.:

(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

Synonyms:(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

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Chemical Property of (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

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Technology Process of (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

There total 1 articles about (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-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: 97.0%

: 98-88-4
benzoyl chloride

: 208338-37-8
(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

: 208338-43-6
(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:: With pyridine; dmap;
DOI:10.1016/S0040-4039(98)00485-7

Reference yield: 89.0%

: 208338-43-6
(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

: 208338-38-9
(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-4-hydroxy-3,4,5-trihydroxymethyl-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:: With hydrogen; palladium on activated charcoal;
DOI:10.1016/S0040-4039(98)00485-7

Reference yield:

: 208338-43-6
(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane

: 156661-55-1
(1S,3S,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(2,2-dimethylpropionyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / H₂; aq. HCl / Pd/C / ethyl acetate / 5 h / 20 °C / 760.05 Torr

2: (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 1.25 h / -78 °C

3: NaClO₂ / 2-methyl-propan-2-ol; H₂O; various solvent(s) / 3 h

4: 30 mg / CH₂Cl₂ / 23 h

5: 75 percent / K₂CO₃ / methanol / 5 h / 20 °C

With hydrogenchloride; sodium chlorite; oxalyl dichloride; hydrogen; potassium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol; 1: Catalytic hydrogenation / 2: Swern oxidation / 3: Pinnick oxidation / 4: Esterification / 5: Substitution;
DOI:10.1021/jo000700m