55287-49-5

Basic information

• Product Name: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE;2-Acetamido-1,3,6-tri-O-benzyl-2-deoxy-a-D-glucopyranoside;PhenylMethyl 2-(AcetylaMino)-2-deoxy-3,6-bis-O-(phenylMethyl)-α-D-glucopyranoside;benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS NO: 55287-49-5
• Molecular Formula: C₂₉H₃₃NO₆
• Molecular Weight: 491.57542
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 55287-49-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 140-141°C
• Boiling Point: 694.641°C at 760 mmHg
• Flash Point: 373.905°C
• Appearance: /
• Density: 1.234g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.94±0.70(Predicted)
• CAS DataBase Reference: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(55287-49-5)
• EPA Substance Registry System: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(55287-49-5)

Safety Data

• Hazardous Substances Data: 55287-49-5(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

InChI:InChI=1/C29H33NO6/c1-21(31)30-26-28(34-18-23-13-7-3-8-14-23)27(32)25(20-33-17-22-11-5-2-6-12-22)36-29(26)35-19-24-15-9-4-10-16-24/h2-16,25-29,32H,17-20H2,1H3,(H,30,31)/t25?,26-,27+,28+,29-/m0/s1

Synthetic route

benzyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside (50908-12-8) + sodium phenyl-methanolate (20194-18-7) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
In N,N-dimethyl-formamide; benzyl alcohol at 90℃; for 1h;	88%

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside (14146-27-1) + benzyl bromide (100-39-0) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
With calcium sulfate; silver(l) oxide In chloroform for 16h;	86%
With tetrabutylammomium bromide; bis(tri-n-butyltin)oxide 1.) toluene, reflux, 4 h, 2.) 80 deg C, 48 h; Yield given. Multistep reaction;

C29H31NO6 → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 2h;	72%

benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (14146-26-0) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride In tetrahydrofuran; diethyl ether at 0℃; for 0.166667h;	60%
With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride In tetrahydrofuran for 0.75h; Yield given;

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside (14146-27-1) + benzyl chloride (100-44-7) → 3,4-di-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (55287-54-2) + benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 3,4,6-tri-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (38416-56-7)

Conditions	Yield
With sodium isopropylate In N,N-dimethyl-formamide at 20℃; for 15h;	A 15% B 50% C 5%

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside (14146-27-1) + benzyl bromide (100-39-0) → 3,4-di-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (55287-54-2) + benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 3,4,6-tri-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside (38416-56-7)

Conditions	Yield
With barium hydroxide octahydrate; barium(II) oxide In N,N-dimethyl-formamide at -5℃; for 4h;	A 8.2% B 39% C 25%
With potassium hydroxide In N,N-dimethyl-formamide at 70 - 90℃;	A 18% B 21% C 25%

(2,2,2-Trichloro-acetyl)-carbamic acid (2R,3S,4R,5R,6S)-5-acetylamino-4,6-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yl ester → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
Stage #1: (2,2,2-Trichloro-acetyl)-carbamic acid (2R,3S,4R,5R,6S)-5-acetylamino-4,6-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yl ester With polystyrene-bound [1,3,2]diazaphosphinane In dichloromethane at 20℃; for 0.166667h; Stage #2: With potassium hydroxide In methanol at 60℃; for 3h;

benzaldehyde dimethyl acetal (1125-88-8) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / p-toluenesulphonic acid / acetonitrile / 60 h / 60 °C 2: 1.) NaH / 1.) THF, 2.) THF 3: NaCNBH3, molecular sieves 3 Angstroem, etheral HCl / tetrahydrofuran / 0.75 h View Scheme

benzyl bromide (100-39-0) + alcoholic potash → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) THF, 2.) THF 2: NaCNBH3, molecular sieves 3 Angstroem, etheral HCl / tetrahydrofuran / 0.75 h View Scheme

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) THF, 2.) THF 2: NaCNBH3, molecular sieves 3 Angstroem, etheral HCl / tetrahydrofuran / 0.75 h View Scheme

benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside (13343-62-9) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 62 percent / p-toluenesulphonic acid / acetonitrile / 60 h / 60 °C 2: 1.) NaH / 1.) THF, 2.) THF 3: NaCNBH3, molecular sieves 3 Angstroem, etheral HCl / tetrahydrofuran / 0.75 h View Scheme

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + acetic anhydride (108-24-7) → Benzyl-2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-desoxy-α-D-glucopyranosid (72489-18-0)

Conditions	Yield
In pyridine	98%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 2-O-Acetyl-3-O-allyl-4,6-O-benzyliden-α-D-glucopyranosyl-trichloracetimidat (143669-73-2) → Benzyl-O-(2-O-acetyl-3-O-allyl-4,6-O-benzyliden-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-desoxy-α-D-glucopyranosid (143669-74-3)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane Ambient temperature;	97%

diphenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl phosphate + benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-glucopyranoside

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane at 20℃; for 7h;	87%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) → N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide (67758-34-3)

Conditions	Yield
With N,N-dimethyl acetamide; silver trifluoromethanesulfonate; triethylamine; 4-Nitrobenzenesulfonyl chloride In dichloromethane 1.) -40 deg C, 2.) -40 -> 0 deg C, 1 h, 3.) 0 deg C, 24 h;	84%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + methanesulfonyl chloride (124-63-0) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(methylsulfonyl)-α-D-glucopyranoside (120596-16-9)

Conditions	Yield
With pyridine at 0 - 5℃;	84%
With pyridine at 0℃; for 24h; Esterification;	77.5%
With pyridine at 4℃; for 24h;	75%
With pyridine at 20℃;

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + Trimethylsilyltriflat → Methyl-2-azido-6-O-benzoyl-2-desoxy-3,4-di-O-trimethylsilyl-β-D-galactopyranosid

Conditions	Yield
With pyridine In dichloromethane	83%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + C46H37O13P → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-glucopyranoside

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; tetramethylurea In dichloromethane for 1h; Ambient temperature;	83%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-xylo-hexo-4-ulopyranoside (129728-97-8)

Conditions	Yield
With acetic anhydride; dimethyl sulfoxide for 140h; Ambient temperature;	82%
With acetic anhydride; dimethyl sulfoxide at 0 - 20℃;	66%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose trichloroacetimidate (161545-19-3) → benzyl O-(3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane; toluene for 2h; Ambient temperature;	80%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + ethyl iodide (75-03-6) → benzyl N-acetyl-3,6-di-O-benzyl-O-ethyl-α-D-glucosamine

Conditions	Yield
Stage #1: benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: ethyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 5h;	80%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + methyl iodide (74-88-4) → benzyl N-acetyl-3,6-di-O-benzyl-O-methyl-α-D-glucosamine

Conditions	Yield
Stage #1: benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 5h;	78%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + (S)-2-chloropropanoic acid (29617-66-1) → benzyl 2-acetamido-3,6-di-O-benzyl-4-O-(D-1-carboxyethyl)-2-deoxy-α-D-glucopyranoside (75263-26-2, 79548-57-5)

Conditions	Yield
With sodium hydride In 1,4-dioxane at 65℃; for 3h;	75%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl bromide (70056-63-2) → Benzyl-2-acetamido-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,6-di-O-benzyl-2-desoxy-α-D-glucopyranosid (83259-23-8)

Conditions	Yield
silver; silicon In dichloromethane	75%
With silver silicate; 4 A molecular sieve 1) CH2Cl2, 1 h, room temp.; 2) 35 deg C, 3 d, CH2Cl2; Yield given. Multistep reaction;

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide (55659-53-5, 77790-47-7, 93381-69-2, 53270-13-6) → benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (74615-20-6)

Conditions	Yield
With 3 A molecular sieve; mercury dichloride In nitromethane; toluene for 118h; Ambient temperature;	73%
With 2,4,6-trimethyl-pyridine; silver trifluoromethanesulfonate In dichloromethane 1.) 0 deg C, 2 h; 2.) overnight, room temp.;	62%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) → Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranosid (73821-89-3)

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane	71%
With 4 A molecular sieve; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃;	55%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + β-D-galactose peracetate (4163-60-4) → Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosid (58700-48-4)

Conditions	Yield
With 4 A molecular sieve; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 3h;	71%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + chlorophosphoric acid diphenyl ester (2524-64-3) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 4-(diphenyl phosphate) (128677-97-4)

Conditions	Yield
With pyridine; dmap In chloroform for 4h; Ambient temperature;	67%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosid (58700-48-4)

Conditions	Yield
With mercury(II) cyanide In benzene for 30h; Heating;	62%
With mercury(II) cyanide In nitromethane; benzene 1.) 60 deg C, 8 h, 2.) r.t., 16 h;	30%
With 4 A molecular sieve; mercury dibromide In 1,2-dichloro-ethane at 80℃; for 36h;

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 2,6-di-O-acetyl-3-O-allyl-4-O-benzyl-D-glucopyranosyl bromide (97576-52-8, 97576-53-9) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,6-di-O-acetyl-3-O-allyl-4-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside (97576-54-0)

Conditions	Yield
With 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane -70 deg C, then RT, 48 h;	55%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-D-glucopyranoside → benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (174148-10-8)

Conditions	Yield
With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve In dichloromethane at 0℃; for 1.5h;	52.3%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + ethyl 2,3,4,6-tetra-O-benzyl-S-(N-tosylimino)-1-thio-β-D-glucopyranoside (216859-55-1) → N-[(2S,4R,5S,6R)-2,4-Bis-benzyloxy-6-hydroxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Conditions	Yield
With Cu2(OTf)2; 4 A molecular sieve; triethylamine; copper(II) oxide In diethyl ether for 0.0833333h; Ambient temperature;	52%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 6-O-acetyl-3-O-benzyl-2-deoxy-4-O-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-2-phthalimido-β-D-glucopyranosyl chloride (92733-49-8) → Benzyl-O-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-O-(6-O-acetyl-3-O-benzyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-desoxy-α-D-glucopyranosid (92733-50-1)

Conditions	Yield
With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane for 24h; Ambient temperature;	50%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 2-O-acetyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α,β-D-glucopyranosyl chloride (88676-27-1, 88676-28-2) → benzyl 2-acetamido-4-O-<2-O-acetyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (88676-33-9)

Conditions	Yield
With 3 A molecular sieve; silver trifluoromethanesulfonate In 1,2-dichloro-ethane for 48h; Ambient temperature;	46%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-α,β-D-glucopyranosyl chloride (140385-12-2) → benzyl 2-acetamido-4-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (92517-07-2)

Conditions	Yield
With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane	41%

3,4,6-tri-O-acetyl-2-O-methyl-α-D-galactopyranosyl bromide (10357-31-0) + benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) → benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-<3,4,6-tri-O-acetyl-2-O-methyl-β-D-galactopyranosyl>-α-D-glucopyranoside (114669-70-4)

Conditions	Yield
With mercury(II) cyanide In acetonitrile for 5h; Ambient temperature;	39.7%

Upstream product

• 14146-27-1 benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 13343-63-0 benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 50908-12-8 benzyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside 
• 20194-18-7 sodium phenyl-methanolate 
• 14146-26-0 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 67758-34-3 N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 74615-20-6 benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 75263-26-2 benzyl 2-acetamido-3,6-di-O-benzyl-4-O-(D-1-carboxyethyl)-2-deoxy-α-D-glucopyranoside 
• 83259-23-8 Benzyl-2-acetamido-4-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-3,6-di-O-benzyl-2-desoxy-α-D-glucopyranosid 
• 79157-02-1 benzyl O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-acetyl-β-D-mannopyranosyl)-(1<*>4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 123809-58-5 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1→3)-1,2,4,6-tetra-O-acetyl-α,β-D-mannopyranose 
• 74615-29-5 Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-2-((2R,3S,4R)-4-acetoxy-2-acetoxymethyl-5-acetylamino-3,4-dihydro-2H-pyran-3-yloxy)-6-acetoxymethyl-tetrahydro-pyran-3-yl ester 
• 74615-26-2 benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1<*>4)-O-(2-acetamido-3,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 92517-07-2 benzyl 2-acetamido-4-O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 97576-54-0 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,6-di-O-acetyl-3-O-allyl-4-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 97576-55-1 benzyl 2-acetamido-4-O-(2-O-acetyl-3-O-allyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 88676-32-8 benzyl 2-acetamido-4-O-<2-O-acetyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 88676-33-9 benzyl 2-acetamido-4-O-<2-O-acetyl-3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 92733-50-1 Benzyl-O-(3,6-di-O-allyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-O-(6-O-acetyl-3-O-benzyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-desoxy-α-D-glucopyranosid 

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FLUORINATED N-ACETYL GLUCOSAMINE ANALOGS AND XYLOSE DERIVATIVES

The present disclosure relates to analogs of N-acetyl glucosamine fluorinated at 4- and/or 6-position(s) and derivatives of xylose at anomeric position for the treatment of a neurological disease, inflammation, cancer and a central nervous system injury.

Preparation of O-Hydroxyethyl and O-Hydroxypropyl Derivatives of D-Glucose and 2-Acetamido-2-deoxy-D-glucose for Studies of Modified Hyaluronic Acid

Some hydroxyethyl and hydroxypropyl derivatives of D-glucose and of 2-acetamido-2-deoxy-D-glucose have been sunthesized for use as reference substances for structural studies of hydroxyethylated and hydroxypropylated hyaluronic acid.Hydroxyethyl and hydroxypropyl substituents were introduced in the 2-O- or 3-O-position of D-glucose and in the 4-O- or 6-O-positions of 2-acetamido-2-deoxy-D-glucose by reaction of suitably protected sugars with either ethylene oxide or propylene oxide.For hydroxyethyl derivatives yields varied between 21 and 74percent and with a substantial portion of the doubly alkylated compounds.For hydroxypropyl derivatives yields varied between 15 and 80percent.Only trace amounts of the doubly alkylated compounds were found.The proportions of the respective derivatives were estimated using GLC-MS.All products were characterized by 1H and 13C NMR spectroscopy.

APPROACHES TO THE SELECTIVE BENZYLATION OF THE PRIMARY HYDROXYL GROUP

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