di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate

Base Information

• Chemical Name: di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate
• CAS No.: 143121-01-1
• Molecular Formula: C₂₃H₃₄O₆
• Molecular Weight: 406.519
• Mol file: 143121-01-1.mol

Synonyms:di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate

Chemical Property of di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate

There total 2 articles about di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate 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:

(R,R)-trans-bis(hydroxymethyl)-1,4-dioxa-5 phenylpentane (58383-35-0) → di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate (143121-01-1)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂ / 0.25 h / -15 °C

2: 1) LDA, 2) DMPU / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 30 min

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/jo00044a051

Reference yield:

acetic acid tert-butyl ester (540-88-5) + Trifluoro-methanesulfonic acid (4R,5R)-2-phenyl-5-trifluoromethanesulfonyloxymethyl-[1,3]dioxolan-4-ylmethyl ester (143104-85-2) → di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate (143121-01-1)

Guidance literature:

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; Yield given. Multistep reaction; 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 30 min;

DOI:10.1021/jo00044a051

Reference yield: 88.0%

di-tert-butyl (4R,5R)-4,5-O-benzylidene-4,5-dihydroxyoctanedioate (143121-01-1) → di-tert-butyl (4R,5R)-4-benzyloxy-5-hydroxyoctanedioate (143104-86-3)

Guidance literature:

With triethylsilane; titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.333333h;

DOI:10.1021/jo00044a051

upstream raw materials:

acetic acid tert-butyl ester

Trifluoro-methanesulfonic acid (4R,5R)-2-phenyl-5-trifluoromethanesulfonyloxymethyl-[1,3]dioxolan-4-ylmethyl ester

(R,R)-trans-bis(hydroxymethyl)-1,4-dioxa-5 phenylpentane

Downstream raw materials:

di-tert-butyl (4R,5R)-4-benzyloxy-5-hydroxyoctanedioate

(4R,5R)-5-(benzyloxy)-7-iodo-4-heptanolide

(4R,5R)-5-(benzyloxy)-7-carboxy-4-heptanolide

Refernces