n-Octyl 3,6-Di-O-(a-D-mannopyranosyl)-b-D-mannopyranoside

Base Information

• Chemical Name: n-Octyl 3,6-Di-O-(a-D-mannopyranosyl)-b-D-mannopyranoside
• CAS No.: 140147-36-0
• Molecular Formula: C26H48 O16
• Molecular Weight: 616.65
• Mol file: 140147-36-0.mol

Synonyms:octyl3,6diO(mannopyranosyl)mannopyranoside;Man1a6[Man1a3]ManOOctyl;nOctyl3,6DiO(aDmannopyranosyl)Dmannopyranoside

Chemical Property of n-Octyl 3,6-Di-O-(a-D-mannopyranosyl)-b-D-mannopyranoside

Chemical Property:

• Vapor Pressure: 2.05E-35mmHg at 25°C
• Melting Point: 111-114℃
• Boiling Point: 870.9°Cat760mmHg
• PKA: 12.72±0.70(Predicted)
• Flash Point: 480.5°C
• PSA: 257.68000
• Density: 1.48g/cm³
• LogP: -4.18820
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Sparingly), Water

Purity/Quality:

98% ^*data from raw suppliers

n-Octyl3,6-Di-O-(α-D-mannopyranosyl)-β-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: n-Octyl 3,6-Di-O-(a-D-mannopyranosyl)-b-D-mannopyranoside is an acceptor for the assay of N-Acetylglucosaminyltransferase-1.It is a useful diagnostic for autosomal recessive congenital muscular dystrophies that can have associated brain and eye abnormalities. An acceptor for the assay of N-Acetylglucosaminyltransferase-1. A useful diagnostic for autosomal recessive congenital muscular dystrophies that can have associated brain and eye abnormalities.

Technology Process of n-Octyl 3,6-Di-O-(a-D-mannopyranosyl)-b-D-mannopyranoside

There total 14 articles about n-Octyl 3,6-Di-O-(a-D-mannopyranosyl)-b-D-mannopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester (205869-99-4) → α-D-Manp-(1->3)-(α-D-Manp)-(1->6)-β-D-Manp-1->O(CH2)7CH3 (140147-36-0)

Guidance literature:

With sodium methylate; In methanol; for 48h; Heating;

DOI:10.1016/S0008-6215(97)00249-8

Reference yield:

1,2:5,6-diacetone-D-glucose (582-52-5) → α-D-Manp-(1->3)-(α-D-Manp)-(1->6)-β-D-Manp-1->O(CH2)7CH3 (140147-36-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) NaH, tetrabutylammonium iodide / 1.) THF, 0 deg C -> room temperature, 2.) THF, 50 deg C, 2 h

2: 81 percent / Dowex 50 (H⁽¹⁺⁾) / H₂O / 2 h / 70 °C

3: 23.2 g / pyridine / CHCl₃ / 24 h / Ambient temperature

4: hydrogen bromide, acetic acid / CH₂Cl₂ / 0.17 h

5: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH₂Cl₂ / 0.5 h

7: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH₂Cl₂, 15 min, 2.) dioxane, water, 20 min

8: 89 percent / pyridine / 1 h

9: 96 percent / NaOMe / methanol; CH₂Cl₂ / 4.5 h

10: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, room temperature, 24 h

11: 53 percent / pyridine / 8 h / Ambient temperature

12: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature

13: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 30 min, 2.) CH₂Cl₂, room temperature, 45 min

14: 84 percent / sodium methoxide / methanol / 48 h / Heating

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; ethanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Dowex 50 (H⁽¹⁺⁾); hydrogen bromide; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; mercury dibromide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; water;

DOI:10.1016/S0008-6215(97)00249-8

Reference yield:

3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside (101475-83-6) → α-D-Manp-(1->3)-(α-D-Manp)-(1->6)-β-D-Manp-1->O(CH2)7CH3 (140147-36-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 81 percent / Dowex 50 (H⁽¹⁺⁾) / H₂O / 2 h / 70 °C

2: 23.2 g / pyridine / CHCl₃ / 24 h / Ambient temperature

3: hydrogen bromide, acetic acid / CH₂Cl₂ / 0.17 h

4: 3.28 g / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 96 percent / molecular sieves 4A, ethanol, N-bromosuccinimide / CH₂Cl₂ / 0.5 h

6: 1.) silver carbonate, molecular sieves 4A, 2.) sodium borohydride / 1.) CH₂Cl₂, 15 min, 2.) dioxane, water, 20 min

7: 89 percent / pyridine / 1 h

8: 96 percent / NaOMe / methanol; CH₂Cl₂ / 4.5 h

9: 1.) molecular sieves 4A, 2.) mercury(II) bromide / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, room temperature, 24 h

10: 53 percent / pyridine / 8 h / Ambient temperature

11: 86 percent / hydrogen, acetic acid / palladium-carbon / ethanol / 2 h / Ambient temperature

12: 1.) molecular sieves 4A, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, room temperature, 30 min, 2.) CH₂Cl₂, room temperature, 45 min

13: 84 percent / sodium methoxide / methanol / 48 h / Heating

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; ethanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; Dowex 50 (H⁽¹⁺⁾); hydrogen bromide; hydrogen; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; mercury dibromide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; chloroform; water;

DOI:10.1016/S0008-6215(97)00249-8

upstream raw materials:

Benzoic acid (2R,3S,4S,5R,6R)-5-acetoxy-2-octyloxy-4-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-6-((2S,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

1,2:5,6-diacetone-D-glucose

3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside

3-O-benzyl-D-glucopyranose

Refernces