Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester
• CAS No.: 157116-97-7
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37
• Mol file: 157116-97-7.mol

Synonyms:Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

Chemical Property of Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

There total 2 articles about Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl 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:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) → Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester (157116-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / Ambient temperature

2: Et₃N / DMAP / CH₂Cl₂ / Ambient temperature

With triethylamine; dmap; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)75797-2

Reference yield:

acetic anhydride (108-24-7) + 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(2-propenyl)-β-D-glucopyranose (104206-19-1) → Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester (157116-97-7)

Guidance literature:

With triethylamine; dmap; In dichloromethane; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)75797-2

Reference yield:

Acetic acid (1R,2S,3R,4R,5R)-4-allyl-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester (157116-97-7) → 2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-(2-hydroxy-ethyl)-3-methyl-6-propyl-cyclohexylmethyl ester

Guidance literature:

Multi-step reaction with 23 steps

2: DEAD-Ph₃P / CH₂Cl₂ / Ambient temperature

3: H₂ / Pd/C / methanol

4: Et₃N / CH₂Cl₂ / -10 °C

5: MeONa / methanol / Ambient temperature

6: diethyl ether / Ambient temperature

7: H₂ / Pd/C / methanol

8: H⁽¹⁺⁾

9: pyridine

10: Swern oxidation

11: MeLi / tetrahydrofuran / -78 °C

12: methylaluminum bis-(4-bromo-2,6-di-tert-butyl-phenoxide) (MABR) / CH₂Cl₂ / -78 °C

13: NaBH₄ / 0.25 h / -20 °C

14: 92 percent / MsCl, Et₃N, DMAP / CH₂Cl₂

15: Bu₄NF / tetrahydrofuran

16: Bu₃P / tetrahydrofuran / 1 h / Ambient temperature

17: 1.) NaIO₄; 2.) Et₃N / 1.) MeOH; 2.) PhCH₃, reflux

18: 86 percent / Hg(OTFA)2 / H₂O; acetone / 1 h / slow addition of the substrate to catalyst

19: 93 percent / MsCl, Et₃N / CH₂Cl₂ / -10 deg C up to RT

20: CeCl₃*7H₂O, NaBH₄ / methanol

21: 98 percent / DMAP/pyridine

22: Me₅Cu₃Li₂ / diethyl ether

23: 96 percent / CAN / acetonitrile; H₂O

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; ammonium cerium(IV) nitrate; tributylphosphine; Me₅Cu₃Li₂; tetrabutyl ammonium fluoride; methyllithium; hydrogen; sodium methylate; hydrogen cation; methanesulfonyl chloride; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; mercury(II) trifluoroacetate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0040-4039(00)75797-2

upstream raw materials:

acetic anhydride

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(2-propenyl)-β-D-glucopyranose

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

Downstream raw materials:

(1R,2R,4R,5R,6R)-5-[3-(4-Methoxy-phenoxy)-propyl]-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

(1S,2S,3S,4R,5R)-2-Allyl-4-[3-(4-methoxy-phenoxy)-propyl]-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

(3S,4R,4aS,6S,7aS)-4a-(2-Hydroxy-2-methyl-propyl)-3-methoxy-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-ol

Benzoic acid (3S,4R,4aS,6S,7aS)-3-methoxy-4a-methoxycarbonylmethyl-4-[3-(4-methoxy-phenoxy)-propyl]-octahydro-cyclopenta[c]pyran-6-yl ester