5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone

Base Information

• Chemical Name: 5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone
• CAS No.: 103927-52-2
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.241
• Mol file: 103927-52-2.mol

Synonyms:5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone

Chemical Property of 5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone

There total 7 articles about 5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone 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: 91.0%

(3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)pentanoate (1583259-35-1) → 5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone (103927-52-2)

Guidance literature:

With water; trifluoroacetic acid; zinc; In toluene; at 20 ℃; for 32h;

DOI:10.1021/ja502205q

Reference yield:

(-)-(2S,3R)-2,3-epoxy-4-(benzyloxy)-1-butanol (78513-07-2) → 5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone (103927-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. ethanol / 8 h / Heating

2: conc. HCl

3: toluene / 12 h / Heating

With hydrogenchloride; In ethanol; toluene;

DOI:10.1055/s-1984-30984

Reference yield:

(3R,4R)-5-Benzyloxy-3,4-dihydroxy-pentanenitrile (99666-07-6,99705-81-4) → 5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone (103927-52-2)

Guidance literature:

Multi-step reaction with 2 steps

1: conc. HCl

2: toluene / 12 h / Heating

With hydrogenchloride; In toluene;

DOI:10.1055/s-1984-30984

upstream raw materials:

D-O-Benzyl-2-deoxyxylic acid

(-)-(2S,3R)-2,3-epoxy-4-(benzyloxy)-1-butanol

(3R,4R)-5-Benzyloxy-3,4-dihydroxy-pentanenitrile

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

Downstream raw materials:

5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-β-D-lyxose

5-benzyloxy-2-desoxy-1-hydroxy-3-hydroxy-α-D-lyxose

(3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one

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

Refernces

• 1、 Takano, Seiichi,Morimoto, Masamichi,Ogasawara, Kunio. "A Facile Synthesis of (S)-5-Benzyloxymethyl-2-oxo-2,5-dihydrofuran via D-5-O-Benzyl-2-deoxyxylono-1,4-lactone". . p. 834 - 835. Retrieved 2007/10/02.