(5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

Base Information

• Chemical Name: (5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one
• CAS No.: 100906-41-0
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252
• Mol file: 100906-41-0.mol

Synonyms:(5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

Chemical Property of (5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one

There total 12 articles about (5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one 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: 86.0%

(Z)-(S)-4-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid (100906-44-3) → (5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one (100906-41-0)

Guidance literature:

With trifluoroacetic acid; at 0 - 20 ℃; for 7h;

DOI:10.1016/0957-4166(96)00424-7

Reference yield: 86.0%

(Z)-4-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid (100906-44-3) → (5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one (100906-41-0)

Guidance literature:

With potassium carbonate; trifluoroacetic acid; for 5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)89235-7

Reference yield:

2-O-benzyl-L-threitol (84379-51-1,84379-52-2,124909-02-0,127000-44-6) → (5S,6S)-5-(benzyloxy)-6-(hydroxymethyl)-5,6-dihydro-2H-pyran-2-one (100906-41-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / TsOH / 12 h / Ambient temperature

2: dimethyl sulfide, N-chlorosuccinimide / 1.) toluene, 6 h, 2.) toluene, from -25 deg C to RT

3: methanol / 20 h

4: 92 percent / 0.5 N aq. LiOH / tetrahydrofuran; methanol / 1 h / Ambient temperature

5: 86 percent / aq. CF₃CO₂H / 7 h / 0 - 20 °C

With lithium hydroxide; N-chloro-succinimide; dimethylsulfide; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; methanol;

DOI:10.1016/0957-4166(96)00424-7

upstream raw materials:

(Z)-4-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid

(Z)-(S)-4-Benzyloxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid

dimethyl 2,3-O-benzylidene-L-tartrate

2-O-benzyl-L-threitol

Downstream raw materials:

Toluene-4-sulfonic acid (2S,3S)-3-benzyloxy-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester

(5S,6S)-5-(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-5,6-dihydro-2H-pyran-2-one

((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-yl)-methanol

((2S,3S,6R)-3-Benzyloxy-6-ethoxy-3,6-dihydro-2H-pyran-2-ylmethoxy)-tert-butyl-dimethyl-silane