(1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane

Base Information

Chemical Name:(1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane
CAS No.:87641-42-7
Molecular Formula:C₁₉H₂₃BrO₆
Molecular Weight:427.292
Hs Code.:

Synonyms:(1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane

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Chemical Property of (1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane

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Technology Process of (1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane

There total 10 articles about (1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-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: 88.0%

: 108-24-7
acetic anhydride

: 98003-87-3
(1S,2R,3R,4R,5R,7R)-4-(4-bromobenzoyloxy)-7-ethyl-2-hydroxy-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane

: 87641-42-7
(1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane

Guidance literature:: With dmap; triethylamine; In dichloromethane; for 1h; Ambient temperature;

Reference yield:

: 53929-15-0,53929-22-9,87641-33-6,87641-34-7,96918-47-7,96997-30-7
1-((3aR,5R,6S,6aR)-6-Methoxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanol

: 87641-42-7
(1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / PCC, mol.sieve / CH₂Cl₂

2: 89 percent / K₂CO₃ / methanol

3: 100 percent / Hydrogen / Pd/C / ethyl acetate / 760 Torr

4: tetrahydrofuran

5: 90 percent / OsO₄, N-Methylmorpholine N-oxide, H₂O / acetone; H₂O / stereoselection: 23/1

6: 82 percent / TsOH,H₂O / CH₂Cl₂

7: 1.) pyridine 2.) DMAP, Et₃N / 1.) CH₂Cl₂ 2.) CH₂Cl₂

With pyridine; dmap; osmium(VIII) oxide; molecular sieve; water; hydrogen; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1016/S0040-4039(00)88188-5

Reference yield:

: 87641-36-9
3,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-glycero-hex-3-enofuranos-5-ulose

: 87641-42-7
(1R,2R,3R,4R,5R,7R)-2-acetoxy-4-(4-bromobenzoyloxy)-7-ethyl-1,3-dimethyl-6,8-dioxabicyclo<3.2.1>octane

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / Hydrogen / Pd/C / ethyl acetate / 760 Torr

2: tetrahydrofuran

3: 90 percent / OsO₄, N-Methylmorpholine N-oxide, H₂O / acetone; H₂O / stereoselection: 23/1

4: 82 percent / TsOH,H₂O / CH₂Cl₂

5: 1.) pyridine 2.) DMAP, Et₃N / 1.) CH₂Cl₂ 2.) CH₂Cl₂

With pyridine; dmap; osmium(VIII) oxide; water; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1016/S0040-4039(00)88188-5