(R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Base Information

• Chemical Name: (R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS No.: 568579-46-4
• Molecular Formula: C₂₃H₃₃BrO₆
• Molecular Weight: 485.415
• Mol file: 568579-46-4.mol

Synonyms:

Chemical Property of (R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

There total 6 articles about (R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-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:

1-hexene (592-41-6,25067-06-5) + Bromo-acetic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (568579-45-3) → (R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (568579-46-4)

Guidance literature:

With triethyl borane; europium(III) trifluoroacetate; oxygen; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(03)00756-1

Reference yield:

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (23202-83-7,2592-42-9) → (R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (568579-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / DCC; 4-DMAP

2: Eu(OTf)3; BEt₃; O₂ / CH₂Cl₂ / -78 °C

With dmap; triethyl borane; europium(III) trifluoroacetate; oxygen; dicyclohexyl-carbodiimide; In dichloromethane; 2: Kharasch reaction;

DOI:10.1016/S0040-4039(03)00756-1

Reference yield:

α-D-xylofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → (R)-4-Bromo-octanoic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (568579-46-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / acetone; H(+1)

2: 70 percent / acetic acid

3: 60 percent / NaH

4: 89 percent / DCC; 4-DMAP

5: Eu(OTf)3; BEt₃; O₂ / CH₂Cl₂ / -78 °C

With dmap; triethyl borane; europium(III) trifluoroacetate; oxygen; hydrogen cation; sodium hydride; acetic acid; dicyclohexyl-carbodiimide; acetone; In dichloromethane; 5: Kharasch reaction;

DOI:10.1016/S0040-4039(03)00756-1

upstream raw materials:

1-hexene

Bromo-acetic acid (3aR,5R,6S,6aR)-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

α-D-xylofuranose