74044-75-0

Basic information

• Product Name: D-Mannitol,1,6-dideoxy-3,4-O-(1-methylethylidene)-
• Synonyms: 1,6-Dideoxy-3,4-O-isopropylidene-d-mannitol
• CAS NO: 74044-75-0
• Molecular Formula: C9H18 O4
• Molecular Weight: 190.24
• Mol File: 74044-75-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: D-Mannitol,1,6-dideoxy-3,4-O-(1-methylethylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Mannitol,1,6-dideoxy-3,4-O-(1-methylethylidene)-(74044-75-0)
• EPA Substance Registry System: D-Mannitol,1,6-dideoxy-3,4-O-(1-methylethylidene)-(74044-75-0)

Safety Data

• Hazardous Substances Data: 74044-75-0(Hazardous Substances Data)

Upstream product

• 63700-05-0 1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol 
• 53754-41-9 1,6-di-O-(p-toluenesulfonyl)-3,4-O-isopropylidene-D-mannitol 
• 172657-94-2 O³,O⁴-isopropylidene-1,6-diiodo-1,6-dideoxy-D-mannitol 
• 3969-59-3 mannitol triacetonide 
• 69-65-8 mannitol 
• 3969-84-4 3,4-di-O-isopropylidene-D-mannitol 
• 60-29-7 diethyl ether 

Downstream Products

• 171524-74-6 1,6-dideoxy-D-mannitol 2,5-di-p-toluenesulfonate 
• 248244-34-0 1,2-bis[(2S,3S,4S,5S)-3,4-dihydroxyl-2,5-dimethylphospholanyl]benzene 
• 259535-67-6 (3aS,4S,6S,6aS)-tetrahydro-2,2,4,6-tetramethyl-5-phenyl-4H-phospholo[3,4-d]-1,3-dioxole 
• 259752-00-6 (2S,3S,4S,5S)-3,4-dihydroxy-2,5-dimethyl-1-phenylphospholane 
• 159716-54-8 (2R,3R,4R,5R)-2,5-dibenzoyloxy-3,4-O-(1-methylethylidene)-3,4-hexanediol 
• 74044-76-1 1,6-dideoxy-3,4-O-isopropylidene-D-mannitol 2,5-di-p-toluenesulfonate 
• 159716-56-0 C₂₀H₂₂O₆ 

Relevant articles and documents

An efficient, one-pot synthesis of fosfomycin dialkyl esters from (R)-2-tosyloxypropanal

(R)-2-Tosyloxypropanal (4) was prepared from D-mannitol in a 7-step sequence (51% overall yield). Addition of dialkyl phosphonates to 4 in the presence of titanium isopropoxide and the subsequent treatment with DBU stereoselectively afforded, in one-pot, fosfomycin dimethyl (5a) and dibenzyl (5b) esters both in 58% isolated yield.

A Novel Chiral Ferrocenyl Phosphine Ligand from Sugar: Applications in Rh-Catalyzed Asymmetric Hydrogenation Reactions

(Matrix Presented) A new chiral ferrocenyl diphosphine ligand 3 was synthesized from readily available D-mannitol. Rh-complex with this ligand showed high enantioselectivity and reactivity in the asymmetric hydrogenation of dehydroamino acid derivatives and itaconic acid derivatives. Up to over 99% ee and 10 000 TON were achieved with this catalytic system.

Highly Flexible Synthetic Routes to Functionalized Phospholanes from Carbohydrates

Highly functionalized phospholanes 15, 17, and 26 and the corresponding diastereomers in which the configurations of the phospholane carbon-2 and carbon-5 are inverted can be readily prepared from D-mannitol by displacement of the appropriate dimesylate or cyclic sulfate with dilithium-phosphide reagents. The diols from which these ligands are prepared can also be converted into diarylphosphinite ligands. A route to related monophosphines bearing hemilabile tert-butylthio groups is also described. Complexes of these ligands and of related deprotected derivatives are potentially useful for enantioselective catalysis in organic and aqueous media.