125158-55-6

Basic information

• Product Name: Furo3,2-doxazole, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3a,5,6,6a-tetrahydro-2-methyl-6-(phenylmethoxy)-, 3aR-3a.alpha.,5.alpha.(R*),6.alpha.,6a.alpha.-
• Synonyms: Furo3,2-doxazole, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3a,5,6,6a-tetrahydro-2-methyl-6-(phenylmethoxy)-, 3aR-3a.alpha.,5.alpha.(R*),6.alpha.,6a.alpha.-
• CAS NO: 125158-55-6
• Molecular Formula: C₁₈H₂₃NO₅
• Molecular Weight: 333.38
• Mol File: 125158-55-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Furo3,2-doxazole, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3a,5,6,6a-tetrahydro-2-methyl-6-(phenylmethoxy)-, 3aR-3a.alpha.,5.alpha.(R*),6.alpha.,6a.alpha.-(CAS DataBase Reference)
• NIST Chemistry Reference: Furo3,2-doxazole, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3a,5,6,6a-tetrahydro-2-methyl-6-(phenylmethoxy)-, 3aR-3a.alpha.,5.alpha.(R*),6.alpha.,6a.alpha.-(125158-55-6)
• EPA Substance Registry System: Furo3,2-doxazole, 5-(2,2-dimethyl-1,3-dioxolan-4-yl)-3a,5,6,6a-tetrahydro-2-methyl-6-(phenylmethoxy)-, 3aR-3a.alpha.,5.alpha.(R*),6.alpha.,6a.alpha.-(125158-55-6)

Safety Data

• Hazardous Substances Data: 125158-55-6(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 67-64-1 acetone 

Downstream Products

• 125158-56-7 2-acetamido-3-O-benzyl-2-deoxy-5,6-O-isopropylidene-D-glucofuranose 
• 149625-44-5 3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-D-glucitol 
• 149625-47-8 2-acetamido-5,6-di-O-acetyl-3-O-benzyl-1,4-(N-benzylimino)-1,2,4-trideoxy-D-galactitol 
• 149625-46-7 3-O-benzyl-1,4-(N-benzylimino)-2-t-butyloxycarbonylamino-1,2,4-trideoxy-5,6-O-isopropylidene-D-glucitol 
• 149625-45-6 3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1,4-di-O-methanesulfonyl-D-glucitol 
• 163707-62-8 1,2-diamino-1,3-di-N,O-benzyl-2,4-N,O-carbonyl-1,2-deoxy-5,6-O-isopropylidene-D-glucitol 
• 163707-63-9 2-amino-3-O-benzyl-2,4-N,O-carbonyl-2-deoxy-5,6-O-isopropylidene-1-O-methanesulfonyl-D-glucitol 
• 163707-55-9 2-acetamido-1,4-di-O-acetyl-3-O-benzyl-2-deoxy-5,6-O-isopropylidene-D-glucitol 
• 163707-61-7 4-O-acetyl-3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-D-galactitol 
• 163707-64-0 5,6-di-O-acetyl-2-amino-3-O-benzyl-2,4-N,O-carbonyl-2-deoxy-1-O-methanesulfonyl-D-glucitol 
• 163707-59-3 2-amino-3-O-benzyl-2,4-N,O-carbonyl-2-deoxy-5,6-O-isopropylidene-1-O-triphenylmethyl-D-galactitol 
• 163707-58-2 4-O-benzyl-5-t-butyloxycarbonylamino-5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-L-xylo-hex-3-ulose 
• 163707-60-6 4-O-acetyl-3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-1-O-triphenylmethyl-D-galactitol 
• 163707-57-1 3-O-benzyl-2-t-butyloxycarbonylamino-2-deoxy-5,6-O-isopropylidene-4-O-methanesulfonyl-1-O-triphenylmethyl-D-glucitol 

Relevant articles and documents

Synthesis of 2-acetamido-2,5-dideoxy-5-phosphoryl-dglucopyranose derivatives: New phospha-sugar analogs of N-acetyl-D-glucosamine

Starting with N-acetyl-D-glucosamine, methyl 2-acetamido-3,6-di-Obenzyl- 2-deoxy-β-D-xylo-hexofuranosid-5-ulose (18) was prepared in 7 steps. The addition reaction of dimethyl phosphonate to 18, followed by deoxygenation of its 5-hydroxy group, provided the 5-deoxy-5-dimethoxyphosphoryl-Dglucofuranoside derivative (21a). The hydride reduction of 21a, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-glucosamine analog (23) having a phosphoryl group in the hemiacetal ring. This was converted into the per-O-acetylated N-acetyl-D-glucosamine phospha-sugar (25), while the same treatment of the 5-deoxy-5- dimethoxyphosphoryl-L-idose dimethyl acetal derivative (13b) afforded the N-acetyl-L-idosamine phospha-sugar (29).

Concise and efficient synthesis of 2-acetamido-2-deoxy-β-D- hexopyranosides of diverse aminosugars from 2-acetamido-2-deoxy-β-D-glucose

The furanose acetonide derivative 1 is readily prepared from 2-acetamido-2-deoxy-D-glucose on a large scale without the need for chromatography. Mesylation of 1 provides an efficient, concise, synthetic route to rare 2-acetamido-2-deoxy-β-D-hexopyranosides (2 and 3) via the corresponding methyl 2-acetamido-2-deoxy-3-O-methanesulfonyl-β-D- glucopyranoside and subsequent inversion of configuration by direct displacement or formation of a 3,4-epoxide. Opening of this epoxide by azide provided a direct route to methyl 2-acetamido-4-amino-2,4,6-trideoxy-β-D- gulopyranoside 4. Benzylation of 1 followed by ring expansion to the glucopyranoside, deoxygenation at C-6, and subsequent displacement of a C-4 triflate permitted the synthesis of methyl 2-acetamido-4-amino-2,4,6-trideoxy- β-D-galactopyranoside 5. Methyl 2-acetamido-2-deoxy-β-D- glucopyranoside available from 1 in quantitative yield was readily converted to methyl 2-acetamido-2-deoxy-β-D-galactopyranoside 6 (>60%) by inversion of configuration at C-4. Introduction of a lactyl substituent at C-3 of oxazoline 1 also provides a facile synthesis of the biologically important muramic acid β-glycoside 7. An interesting reaction to convert 2-acetamido-2-deoxyhexopyranosides to the corresponding 2-deoxy-2-tetrazole is also reported.

Synthesis of 2-acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol and -D-glucitol for evaluation as glycosidase inhibitors

The title compounds, galacto-1 and gluco-2, were synthesised from N-acetyl-D-glucosamine via a common 1,4-diol intermediate that underwent transformations involving either a single or double inversion of stereochemistry at C-4, respectively. In the double

Synthesis of 2-acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol, a new hexosaminidase inhibitor

2-Acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol was synthesised from 2-acetamido-2-deoxy-D-glucose in 12 steps and was shown to be a modest hexosaminidase inhibitor.