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

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

• 100-39-0 benzyl bromide 
• 79999-47-6 tri-O-(tert-butyldimethylsilyl)-D-glucal 
• 74-88-4 methyl iodide 
• 64978-35-4 1,5-anhydro-3,4,6-tri-O-benzyl-1,2-dideoxy-1-phenylsulfonyl-D-arabino-hex-1-enitol 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 917-54-4 methyllithium 
• 221183-87-5 C₃₀H₃₄O₄ 
• 75-24-1 trimethylaluminum 
• 126709-14-6 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 64978-34-3 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranosyl sulfone 
• 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 

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.

Synthesis of C-1 alkyl and aryl glycals from pyranosyl or furanosyl chlorides by treatment with organolithium reagents

Glycosyl chlorides, with ether or isopropylidene acetal protecting groups, readily available from furanoses or pyranoses, can be conveniently transformed into C-1 alkyl or aryl glycals by reaction with alkyl or aryl organolithium reagents.

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

Formation of C-Glycosides by Polarity Inversion at the Anomeric Centre

Alkylation of 1-lithio trisubstituted glycals obtained via the corresponding 1-tributylstannyl derivatives constitutes a novel entry into C-glycosides.