105938-02-1

Basic information

• Product Name: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol
• Synonyms: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol
• CAS NO: 105938-02-1
• Molecular Weight: 430.544
• Mol File: 105938-02-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol(105938-02-1)
• EPA Substance Registry System: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol(105938-02-1)

Safety Data

• Hazardous Substances Data: 105938-02-1(Hazardous Substances Data)

Upstream product

• 64978-34-3 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranosyl sulfone 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 13265-84-4 D-glucal 
• 221183-86-4 Acetic acid (1R,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-pent-4-enyl ester 
• 102208-53-7 (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 
• 60933-68-8 3,4,6-tri-O-benzyl-β-D-arabinofuranoside 
• 75-24-1 trimethylaluminum 
• 126709-14-6 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 
• 221183-87-5 C₃₀H₃₄O₄ 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 917-54-4 methyllithium 
• 64978-35-4 1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol 
• 74-88-4 methyl iodide 
• 100-39-0 benzyl bromide 

Downstream Products

• 105938-03-2 (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol 

Relevant articles and documents

Expeditious entry to C-alkyl and C-aryl pyranoid glycals: Reaction of anomeric glycosyl chlorides with organolithiums

Treatment of ether-substituted glycopyranosyl chlorides with organolithium reagents gives the corresponding C-glycals in acceptable to good yields.

Glycosylidene carbenes. Part 29. Insertion into B-C and Al-C bonds: Glycosylborinates, -boranes, and -alanes

Insertion of the glycosylidene carbenes derived from the diazirines 1, 14, and 15 into the B-alkyl bond of the B-alkyl-9-oxa-10- borabicyclo[3.3.2]decanes 5, 6, and 7 yielded the stable glycosylborinates 8/9 (55%, 55:45), 10/11 (31%, 65:35), 12/13 (47%, 60:40), 16/17 (55%, 55:45), 18/19 (47%, 45:55), and 20/21 (31%, 30:70). Crystal-structure analysis of 17 and NOEs of 9 and 19 show that 17, 9, and 19 adopt similar conformations. The glycosylborinates are stable under acidic, basic and thermal conditions. The unprotected glycosylborinate 25 was obtained in 80% by hydrogenolysis of 12. Insertion of the glycosylidene carbene derived from the diazirine 1 into a B- C bond of BEt3, BBu3, and BPh3 led to unstable glycosylboranes that were oxidised to yield the hemiacetals 29 (55%), 31 (45%), and 33 (48%), respectively, besides the glucals 30 (13%), 32 (20%), and 34 (20%), respectively. Insertion of the glycosylidene carbenes derived from 14 and 15 into a B-C bond of BEt3 led exclusively to hemiacetals; only 15 yielding traces of the glucal 40 besides the hemiacetal 39. The glycosylidene carbene derived from 1 reacted with Al((i)Bu)3 and AlMe3 to generate reactive glycosylalanes that were hydrolysed, yielding the C-glycosides 46 (21%) and 49 (30%), respectively, besides the glucals 48 (26%) and 51 (30%); deuteriolysis instead of protonolysis led to the monodeuterio analogues of 46 and 49, respectively, which possess an equatorial 2H-atom at the anomeric center.

PREPARATION AND USE OF LITHIATED GLYCALS: VINYLIC DEPROTONATION VERSUS TIN-LITHIUM EXCHANGE FROM 1-TRIBUTYLSTANNYL GLYCALS

Methods for preparing glycals lithiated at the C-1 atom by either direct vinylic deprotonation or by tin-lithium exchange from the corresponding 1-tri-n-butylstannyl glycals are described.Alkylation of these lithiated anions wih various electrophiles lead