78508-91-5

Basic information

• Product Name: 5-benzyloxy-2-hydroxy-3-hydroxy-D-ribonolactone
• Synonyms: 5-benzyloxy-2-hydroxy-3-hydroxy-D-ribonolactone
• CAS NO: 78508-91-5
• Molecular Weight: 238.24
• Mol File: 78508-91-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-benzyloxy-2-hydroxy-3-hydroxy-D-ribonolactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-benzyloxy-2-hydroxy-3-hydroxy-D-ribonolactone(78508-91-5)
• EPA Substance Registry System: 5-benzyloxy-2-hydroxy-3-hydroxy-D-ribonolactone(78508-91-5)

Safety Data

• Hazardous Substances Data: 78508-91-5(Hazardous Substances Data)

Upstream product

• 85846-80-6 5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 157453-65-1 (3R,4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxy-dihydrofuran-2-one 
• 4799-68-2 3-benzyloxypropan-1-ol 
• 19790-60-4 3-Benzyloxypropanal 
• 1583259-32-8 (2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldimethylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 
• 1583259-07-7 (R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal 
• 5336-08-3 D-Ribono-1,4-lactone 

Downstream Products

• 5336-08-3 D-Ribono-1,4-lactone 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 72605-53-9 γ-benzyloxymethyl-α,β-butenolide 
• 147410-05-7 Toluene-4-sulfonic acid (3S,5S)-5-benzyloxymethyl-2-oxo-tetrahydro-furan-3-yl ester 
• 147410-01-3 (S)-5-Benzyloxymethyl-3-tosyloxy-2(5H)-furanone 
• 147410-02-4 (3S,5S)-5-Hydroxymethyl-3-tosyloxy-2(3H)-dihydrofuranone 
• 85846-80-6 (-)-5-O-benzyl-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 147410-04-6 5-O-Benzyl-2-O-tosyl-D-ribonolactone 
• 78508-94-8 5-O-benzyl-2,3-O-ethoxymethylene-D-ribonolactone 

Relevant articles and documents

High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues

A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.

A SHORT SYNTHESYS OF (S)-5-HYDROXYMETHYL-(5H)-FURAN-2-ONE AND DERIVATIVES FROM D-RIBONOLACTONE

We describe a short synthesis of (S)-5-hydroxymethyl-(5H)-furan-2-one and some 5-O-derivatives, which are being used as key starting products for the synthesis of several antileukaemic lignan lactones, from D-ribonolactone.