3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE

Base Information

• Chemical Name: 3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE
• CAS No.: 134877-40-0
• Molecular Formula: C12H12 O5
• Molecular Weight: 236.22
• Mol file: 134877-40-0.mol

Synonyms:4H-1,3-Dioxolo[4,5-c]pyran,D-ribonic acid deriv.; 3,4-O-Benzylidene-D-ribonic-d-lactone

Chemical Property of 3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE

Chemical Property:

• Boiling Point: 471.9±45.0 °C(Predicted)
• PKA: 11.95±0.40(Predicted)
• PSA: 64.99000
• Density: 1.377±0.06 g/cm3(Predicted)
• LogP: 0.38690

Purity/Quality:

99% ^*data from raw suppliers

3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE

There total 3 articles about 3,4-O-BENZYLIDENE-D-RIBO-1,5-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: 87.0%

benzaldehyde (100-52-7) + D-Ribono-1,4-lactone (5336-08-3) → 3,4-O-benzylidene-D-ribonic-δ-lactone (134877-40-0)

Guidance literature:

With hydrogenchloride; for 7h;

DOI:10.1016/j.tetasy.2004.12.008

Reference yield: 59.0%

benzaldehyde (100-52-7) + (4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-dihydro-furan-2-one (2782-09-4,3327-63-7,5336-08-3,13280-76-7,15384-34-6,15384-37-9,17676-01-6,18423-66-0,51532-86-6,68035-75-6,104196-15-8,133908-85-7) → 3,4-O-benzylidene-D-ribonic-δ-lactone (134877-40-0)

Guidance literature:

With hydrogenchloride; at 25 ℃; for 0.5h;

DOI:10.1016/0008-6215(91)80010-K

Reference yield: 26.0%

3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone (473596-05-3) → 3,4-O-benzylidene-D-ribonic-δ-lactone (134877-40-0)

Guidance literature:

With Decaborane; In methanol; at 20 ℃; for 12h;

DOI:10.1039/b201794f

upstream raw materials:

benzaldehyde

(4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-dihydro-furan-2-one

D-Ribono-1,4-lactone

3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone

Downstream raw materials:

((3aR,7R,7aS)-6-Oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-carbamic acid benzyl ester

2-Azido-2-deoxy-3,4-O-benzylidene-1,5-D-ribonolactone

(5S)-(5-hydroxymethyl-2-oxo-2,5-dihydrofuran-3-yl)carbamic acid benzyl ester

2-Amino-2-deoxy-3,4-O-benzylidene-1,5-D-ribonolactone

Refernces

• 1、 Jeong, Yeon Joo,Lee, Ji Hee,Park, Eun Soo,Yoon, Cheol Min. "Efficient and chemoselective cleavage of TBS ethers by a sub-stoichiometric amount of decaborane". . p. 1223 - 1225. Retrieved 2007/10/03.
• 2、 Ariza, Jesus,Font, Josep,Ortuno, Rosa M.. "An efficient and concise entry to (-)-4,5-dihydroxy-d-threo-l norvaline. Formal synthesis of clavalanine". . p. 1979 - 1982. Retrieved 2007/10/02.