3-O-Methyl-alpha-D-glucopyranose

Base Information

• Chemical Name: 3-O-Methyl-alpha-D-glucopyranose
• CAS No.: 13224-94-7
• Molecular Formula: C7H14O6
• Molecular Weight: 194.185
• Hs Code.: 29400090
• European Community (EC) Number: 236-197-7
• UNII: PX96ZE0GYS
• DSSTox Substance ID: DTXSID8037629
• Nikkaji Number: J213.759C
• Mol file: 13224-94-7.mol

Synonyms:3-O-Methyl-alpha-D-glucopyranose;13224-94-7;3-O-Methyl-a-D-glucopyranose;3-O-Methyl-D-glucopyranose;(2S,3R,4S,5R,6R)-6-(Hydroxymethyl)-4-methoxytetrahydro-2H-pyran-2,3,5-triol;(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-4-methoxyoxane-2,3,5-triol;MFCD00063266;PX96ZE0GYS;.alpha.-D-Glucopyranose, 3-O-methyl-;EINECS 236-197-7;alpha-D-Glucopyranose, 3-O-methyl-;3-o-methyl-|A-d-glucopyranose;UNII-PX96ZE0GYS;3-o-methyl-alpha-d-glucose;SCHEMBL1696452;a-D-Glucopyranose,3-O-methyl-;DTXSID8037629;GEO-01844;3-O-Methyl-D-glucopyranose, >=98%;AKOS005255099;3-O-METHYL-.ALPHA.-D-GLUCOSE;HY-W145482;AS-60161;Glucopyranose, 3-O-methyl-, .alpha.-D-;3-O-METHYL-.ALPHA.-D-GLUCOPYRANOSE;CS-0214416;E80633;A888317;W-200101;WURCS=2.0/1,1,0/[a2122h-1a_1-5_3*OC]/1/;(2S*,3R*,4S*,5R*,6R*)-6-Hydroxymethyl-4-methoxy-tetrahydro-pyran-2,3,5-triol;ZB1

Chemical Property of 3-O-Methyl-alpha-D-glucopyranose

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 167-169 °C(lit.)
• Refractive Index: 1.548
• Boiling Point: 406.3 °C at 760 mmHg
• PKA: 12.05±0.70(Predicted)
• Flash Point: 199.5 °C
• PSA: 99.38000
• Density: 1.47g/cm³
• LogP: -2.56730
• Storage Temp.: 0-6°C
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 194.07903816
• Heavy Atom Count: 13
• Complexity: 163

Purity/Quality:

GC ≥98% ^*data from raw suppliers

3-O-Methyl-D-glucopyranose 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1C(C(OC(C1O)O)CO)O
• Isomeric SMILES: CO[C@H]1[C@@H]([C@H](O[C@@H]([C@@H]1O)O)CO)O

Technology Process of 3-O-Methyl-alpha-D-glucopyranose

There total 13 articles about 3-O-Methyl-alpha-D-glucopyranose 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:

(3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol (97834-06-5) → 3-O-methyl-D-glucose (13224-94-7) + 3-O-methyl-β-D-glucopyranose (13224-95-8)

Guidance literature:

With Amberlite IR-120 (H⁺ form); In water; at 80 ℃; for 16h; Overall yield = 100 percent; Overall yield = 39.6 mg;

DOI:10.1002/anie.201906577

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-O-methyl-D-glucose (13224-94-7)

Guidance literature:

(methylation);

DOI:10.1016/S0008-6215(00)81150-7

Reference yield:

→ 3-O-methyl-D-glucose (13224-94-7)

Guidance literature:

upstream raw materials:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

(3aR,5R,6S,6aR)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methoxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]-dioxol

1,2:5,6-di-O-isopropylidene-α-D-gulose

5-[2,2-dimethyl-(4R)-1,3-dioxolan-4-yl]-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-6-yl methyl ether

Downstream raw materials:

Benzoic acid (S)-((4S,4aS,8aR,9R,9aR,10aR)-9-methoxy-7,7-dimethyl-hexahydro-1,3,6,8,10-pentaoxa-anthracen-4-ylcarbamoyl)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid (S)-((4R,4aS,8aR,9R,9aR,10aR)-9-methoxy-7,7-dimethyl-hexahydro-1,3,6,8,10-pentaoxa-anthracen-4-ylcarbamoyl)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid (S)-[(4S,4aS,6R,7R,8R,8aR)-7-acetoxy-6-(2,2-dimethyl-propionyloxymethyl)-8-methoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid (S)-[(4R,4aS,6R,7R,8R,8aR)-7-acetoxy-6-(2,2-dimethyl-propionyloxymethyl)-8-methoxy-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Refernces

• 1、 De,K.K.,Timell,T.E.. "-". . p. 72 - 77. Retrieved 1967.
• 2、 Patroni, Joseph J.,Stick, Robert V.,Tilbrook, D. Matthew G.,Skelton, Brian W.,White, Allan H.. "The Synthesis and Reactivity of Cyclic Thiocarbonates Derived from Some Carbohydrate 1,2-Diols". . p. 2127 - 2141. Retrieved 2007/10/02.