(2S,3R)-1(2H)-PYRIDINECARBOXYLIC ACID, 3,6-DIHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-, 1,1-DIMETHYLETHYL ESTER

Base Information

• Chemical Name: (2S,3R)-1(2H)-PYRIDINECARBOXYLIC ACID, 3,6-DIHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-, 1,1-DIMETHYLETHYL ESTER
• CAS No.: 505085-66-5
• Molecular Formula: C11H19NO4
• Molecular Weight: 229.27300
• Mol file: 505085-66-5.mol

Synonyms:(2S,3R)-1(2H)-PYRIDINECARBOXYLIC ACID, 3,6-DIHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-, 1,1-DIMETHYLETHYL ESTER;(2S,3R)-3-Hydroxy-2-hydroxymethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester;tert-butyl (2S,3R)-3-hydroxy-2-(hydroxymethyl)-1,2,3,6-tetrahydropyridin-1-carboxylate;

Chemical Property of (2S,3R)-1(2H)-PYRIDINECARBOXYLIC ACID, 3,6-DIHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-, 1,1-DIMETHYLETHYL ESTER

Chemical Property:

• PSA: 70.00000
• LogP: 0.45300

Purity/Quality:

(2S,3R)-1(2H)-PYRIDINECARBOXYLIC ACID-3,6-DIHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-1,1-DIMETHYLETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3R)-1(2H)-PYRIDINECARBOXYLIC ACID, 3,6-DIHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-, 1,1-DIMETHYLETHYL ESTER

There total 13 articles about (2S,3R)-1(2H)-PYRIDINECARBOXYLIC ACID, 3,6-DIHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-, 1,1-DIMETHYLETHYL 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: 94.0%

tert-butyl (4aS,8aR)-2,2-dimethyl-4,4a,6,8a-tetrahydro-5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate (505085-63-2) → (-)-(2S,3R)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylic tert-butyl ester (505085-66-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 2h;

DOI:10.1021/jm0495881

Reference yield:

C15H23NO6 (949104-01-2) → (-)-(2S,3R)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylic tert-butyl ester (505085-66-5)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 4h;

DOI:10.1021/ol7014847

Reference yield:

C24H35NO6S2 (949103-95-1) → (-)-(2S,3R)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine-1-carboxylic tert-butyl ester (505085-66-5)

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid / H₂O / 1 h / 50 °C

2: 1.86 g / pyridine / 20 °C

3: 95 percent / DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

4: 85 percent / silver oxide; p-toluenesulfonyl chloride / tetrahydrofuran / 40 °C

5: 76 percent / hydrogen / Raney nickel / ethanol / 2 h / 0 °C

6: sodium methoxide / methanol / 4 h / 20 °C

With pyridine; hydrogen; sodium methylate; acetic acid; p-toluenesulfonyl chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 6: Zemplen deacetylation;

DOI:10.1021/ol7014847

upstream raw materials:

tert-butyl (4aS,8aR)-2,2-dimethyl-4,4a,6,8a-tetrahydro-5H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate

C₁₅H₂₃NO₆

C₂₄H₃₅NO₆S₂

C₂₅H₃₅NO₈S₂

Downstream raw materials:

C₄₃H₅₅NO₄Si₂

C₄₃H₅₇NO₆Si₂