2-O-Benzyl-D-arabinoic acid γ-lactone

Base Information

• Chemical Name: 2-O-Benzyl-D-arabinoic acid γ-lactone
• CAS No.: 34685-51-3
• Molecular Formula: C₁₂H₁₄O₅
• Molecular Weight: 238.24
• Mol file: 34685-51-3.mol

Synonyms:

Chemical Property of 2-O-Benzyl-D-arabinoic acid γ-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-Benzyl-D-arabinoic acid γ-lactone

There total 2 articles about 2-O-Benzyl-D-arabinoic acid γ-lactone 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:

(Z)-2-Benzyloxy-1-ethylthio-1-(trimethylsiloxy)ethene (129320-44-1) → (3R,4R,5S)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one (132333-80-3,34685-51-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / tin(II) triflate, (S)-1-methyl-2-<(piperidin-1-yl)methyl>pyrrolidine, dibutyltindiacetate / CH₂Cl₂ / -78 °C

2: N-methylmorpholineoxide, OsO₄ / acetone; H₂O / Ambient temperature

With osmium(VIII) oxide; tin(II) trifluoromethanesulfonate; dibutyltin diacetate; (S)-1-methyl-2-<(piperidin-1-yl)-methyl>pyrrolidine; 4-methylmorpholine N-oxide; In dichloromethane; water; acetone;

Reference yield:

S-ethyl (2R,3R)-2-benzyloxy-3-hydroxy-4-pentenethioate (132333-72-3) → (3R,4R,5R)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-pyran-2-one (132333-79-0) + (3R,4R,5S)-3-Benzyloxy-4-hydroxy-5-hydroxymethyl-dihydro-furan-2-one (132333-80-3,34685-51-3)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; Yield given. Yields of byproduct given; Ambient temperature;

upstream raw materials:

S-ethyl (2R,3R)-2-benzyloxy-3-hydroxy-4-pentenethioate

(Z)-2-Benzyloxy-1-ethylthio-1-(trimethylsiloxy)ethene

Refernces