L-threo-Hexonic acid, 2,4-dideoxy-3-O-methyl-, delta-lactone (9CI)

Base Information

• Chemical Name: L-threo-Hexonic acid, 2,4-dideoxy-3-O-methyl-, delta-lactone (9CI)
• CAS No.: 310883-86-4
• Molecular Formula: C7H12 O4
• Molecular Weight: 160.17
• Mol file: 310883-86-4.mol

Synonyms:L-threo-Hexonic acid, 2,4-dideoxy-3-O-methyl-, delta-lactone (9CI)

Chemical Property of L-threo-Hexonic acid, 2,4-dideoxy-3-O-methyl-, delta-lactone (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-threo-Hexonic acid, 2,4-dideoxy-3-O-methyl-, delta-lactone (9CI)

There total 7 articles about L-threo-Hexonic acid, 2,4-dideoxy-3-O-methyl-, delta-lactone (9CI) 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: 84.0%

(6R)-4-methoxy-6-(benzyloxymethyl)-5,6-dihydro-2H-pyran-2-one (296785-14-3) → (4R,6R)-6-hydroxymethyl-4-methoxy-tetrahydro-2H-pyran-2-one (310883-86-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 12h;

DOI:10.1039/b407240e

Reference yield:

(4R,6R)-6-(benzyloxymethyl)-4-methoxy-tetrahydro-2H-pyran-2-one (296785-16-5) → (4R,6R)-6-hydroxymethyl-4-methoxy-tetrahydro-2H-pyran-2-one (310883-86-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃;

DOI:10.1002/1521-3773(20000717)39:14<2533::AID-ANIE2533>3.0.CO;2-B

Reference yield:

tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate (147849-63-6) → (4R,6R)-6-hydroxymethyl-4-methoxy-tetrahydro-2H-pyran-2-one (310883-86-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / chlorotrimethylsilane / CH₂Cl₂ / 24 h / 0 °C

2: 86 percent / H₂ / Raney-Ni / propan-2-ol / 3 h / 20 °C / 760 Torr

3: 242 mg / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C / 760.05 Torr

With chloro-trimethyl-silane; hydrogen; palladium on activated charcoal; nickel; In dichloromethane; ethyl acetate; isopropyl alcohol;

DOI:10.1021/ja002356g

upstream raw materials:

(4R,6R)-6-(benzyloxymethyl)-4-methoxy-tetrahydro-2H-pyran-2-one

(6R)-4-methoxy-6-(benzyloxymethyl)-5,6-dihydro-2H-pyran-2-one

(R)-(3-benzyloxy-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxin-4-one

(R)-6-Benzyloxymethyl-dihydro-pyran-2,4-dione

Downstream raw materials:

(2R,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-[2-(trimethylsilyloxyethyl)]-4-(triphenylsilyloxy)-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]-methyl-4-methoxy-2-(triethylsilyloxy)-6-(triethylsilyloxymethyl)-tetrahydro-2H-pyran-2-ol

(2S,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-(2-trimethylsilyloxyethyl)-4-triphenylsilyloxy-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]methyl-4-methoxy-6-triethylsilyloxymethyl-tetrahydro-2H-pyran-2-ol

Refernces

• 1、 Evans, David A.,Cee, Victor J.,Smith, Thomas E.,Fitch, Duke M.,Cho, Patricia S.. "Asymmetric synthesis of phorboxazole B - Part I: Synthesis of the C20-C38 and C39-C46 subunits". . p. 2533 - 2536. Retrieved 2007/10/03.