L-Ribono-1,4-lactone

Base Information

• Chemical Name: L-Ribono-1,4-lactone
• CAS No.: 133908-85-7
• Molecular Formula: C5H8O5
• Molecular Weight: 148.116
• Mol file: 133908-85-7.mol

Synonyms:L-Ribono-1,4-lactone

Chemical Property of L-Ribono-1,4-lactone

Chemical Property:

• Melting Point: 115 - 116 °C (acetone)
• PSA: 86.99000
• LogP: -2.37410

Purity/Quality:

97% ^*data from raw suppliers

L-Ribono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: L-Ribono-1,4-lactone is an analog of D-Ribonolactone which is used as an inhibitor of β-galactosidase of E. coli.

Technology Process of L-Ribono-1,4-lactone

There total 14 articles about L-Ribono-1,4-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:

calcium D-ribonate (5346-83-8,7546-24-9,18905-33-4,22373-09-7,56512-56-2,62102-50-5,72656-08-7,74440-84-9,76386-31-7,123249-13-8,123277-10-1,133480-82-7,133480-83-8) → (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) + D-Ribono-1,4-lactone (5336-08-3)

Guidance literature:

With sulfuric acid; In water; Yield given;

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

Reference yield:

Adonitol (488-81-3) → ribonolactone (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) + DL-arabinonic acid-4-lactone (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)

Guidance literature:

With 1-Phenylbut-1-en-3-one; rhodium hydrido (PEt₃)3 complex; In N,N-dimethyl-formamide; at 80 ℃; for 5h; Yield given. Yields of byproduct given;

DOI:10.1055/s-1998-1705

Reference yield:

Adonitol (488-81-3) → ribonolactone (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) + DL-arabinonic acid-4-lactone (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)

Guidance literature:

With 1-Phenylbut-1-en-3-one; rhodium hydrido (PEt₃)3 complex; In N,N-dimethyl-formamide; at 80 ℃; for 5h; Yield given. Yields of byproduct given;

DOI:10.1055/s-1998-1705

upstream raw materials:

L-ribonic acid

(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

D-Ribose

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Downstream raw materials:

3-hydroxy-2-pyrone

2-furanoic acid

(+/-)-Tri-O-acetylarabono-1,4-lactone

3,4-O-benzylidene-D-ribonic-δ-lactone

Refernces

• 1、 Fleming, Ian,Ghosh, Sunil K.. "Stereocontrol in organic synthesis using silicon-containing compounds. Syntheses of (±)-2-deoxyribonolactone and (±)-arabonolactone". . p. 2711 - 2720. Retrieved 2007/10/03.
• 2、 Fleming, Ian,Ghosh, Sunil K.. "Stereoselective Samarium(II)-induced Coupling of β-Silylacrylic Esters: a Synthesis of (+/-)-2-Deoxyribonolactone". . p. 1775 - 1777. Retrieved 2007/10/02.