(3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

Base Information

• Chemical Name: (3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate
• CAS No.: 1583260-38-1
• Molecular Formula: C₂₄H₃₇F₂NO₅
• Molecular Weight: 457.558
• Mol file: 1583260-38-1.mol

Synonyms:(3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

Chemical Property of (3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

There total 1 articles about (3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 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: 59.0%

3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal + 2,2-difluoro-2-bromoacetic acid isopropyl ester (134682-34-1) → (3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate (1583260-38-1) + (3S,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate (1583260-39-2)

Guidance literature:

With zinc; In tetrahydrofuran; for 2h; diastereoselective reaction; Reflux;

DOI:10.1021/ja502205q

Reference yield: 85.0%

(3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate (1583260-38-1) → (4R,5R)-5-(benzyloxymethyl)-3,3-difluoro-4-hydroxy-dihydrofuran-2(3H)-one (1583260-40-5)

Guidance literature:

(3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate; With acetic acid; zinc; In ethanol; water; ethyl acetate; at 20 ℃; for 4h; Sonication;

With acetic acid; In acetonitrile; for 48h; Reflux;

DOI:10.1021/ja502205q

Reference yield:

(3R,4R)-isopropyl 5-(benzyloxy)-2,2-difluoro-3-hydroxy-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate (1583260-38-1) → (2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-(methylsulfonyloxy)tetrahydrofuran-3-yl benzoate (1583260-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: zinc; acetic acid / ethyl acetate; ethanol; water / 4 h / 20 °C / Sonication

1.2: 48 h / Reflux

2.1: pyridine / dichloromethane / 1 h / 0 °C

3.1: lithium tri-t-butoxyaluminum hydride / diethyl ether; tetrahydrofuran / 1 h / 0 °C

3.2: 20 °C

4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C

With pyridine; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate;

DOI:10.1021/ja502205q

upstream raw materials:

2,2-difluoro-2-bromoacetic acid isopropyl ester

Downstream raw materials:

(4R,5R)-5-(benzyloxymethyl)-3,3-difluoro-4-hydroxy-dihydrofuran-2(3H)-one

(2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-oxo-tetrahydrofuran-3-yl benzoate

(2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-(methylsulfonyloxy)tetrahydrofuran-3-yl benzoate

(2R,3R)-2-(benzyloxymethyl)-4,4-difluoro-5-iodo-tetrahydrofuran-3-yl benzoate