D-Glucopyranose, pentaacetate

Base Information

• Chemical Name: D-Glucopyranose, pentaacetate
• CAS No.: 83-87-4
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.344
• European Community (EC) Number: 617-497-0
• DSSTox Substance ID: DTXSID70232114
• Nikkaji Number: J885.970A
• Mol file: 83-87-4.mol

Synonyms:83-87-4;D-Glucopyranose, pentaacetate;(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate;Peracetylglucose;Pentaacetyl-D-glucose;1,2,3,4,6-Penta-O-acetyl-D-glucopyranose;Pentaacetyl-dextro-glucose;Penta-O-acetyl-D-glucopyranose;alpha,beta-D-Glucose Pentaacetate;[(2R,3R,4S,5R)-3,4,5,6-tetraacetyloxyoxan-2-yl]methyl acetate;1,2,3,4,6-Pentaacetyl-D-glucose;Glucose 1,2,3,4,6-pentaacetate, D-;C16H22O11;glucopyranose pentaacetate;D-Glucopyranose pentaacetate;ETHYL4-BENZYLBENZOATE;SCHEMBL313806;D-Glucose pentaacetate;Glucopyranose pentaacetate;Glucose pentaacetate;DTXSID70232114;LPTITAGPBXDDGR-IWQYDBTJSA-N;CS-M3449;MFCD00080787;AKOS025310965;DS-9971;10.14272/LPTITAGPBXDDGR-IWQYDBTJSA-N;F20314;EN300-7405456;1,2,3,4,6-penta-o-acetyl-alpha,beta-d-glucose;10.14272/LPTITAGPBXDDGR-IWQYDBTJSA-N.1;A864205;doi:10.14272/LPTITAGPBXDDGR-IWQYDBTJSA-N;doi:10.14272/LPTITAGPBXDDGR-IWQYDBTJSA-N.1;1,2,3,4,6-Penta-O-acetyl-alpha,beta-D-glucopyranose;(3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayltetraacetate;[(2R,3R,4S,5R)-3,4,5,6-TETRAKIS(ACETYLOXY)OXAN-2-YL]METHYL ACETATE

Chemical Property of D-Glucopyranose, pentaacetate

Chemical Property:

• Melting Point: 130-132 ºC
• Boiling Point: 452 °C
• PSA: 140.73000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: -0.36740
• Storage Temp.: 0-6°C
• Solubility.: chloroform: 0.1 g/mL, clear, colorless
• Water Solubility.: chloroform: 0.1 g/mL, clear, colorless
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 390.11621151
• Heavy Atom Count: 27
• Complexity: 599

Purity/Quality:

98%, ^*data from raw suppliers

alpha,beta-D-Glucose pentaacetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Description: Glucose pentaacetate is odorless with a bitter flavor. May be synthesized by acetylation of glucose using any number of techniques, including: ZnCl2 and pyridine, sodium acetate, and acetic anhydride and pyridine.

Technology Process of D-Glucopyranose, pentaacetate

There total 52 articles about D-Glucopyranose, pentaacetate 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: 59.0%

1,3,4,6-tetra-O-acetyl-2-O-trityl-α-D-galactopyranose (130052-61-8) + 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl thiocyanate (130052-60-7) → 1,3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranose (130052-63-0) + Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-isothiocyanato-tetrahydro-pyran-4-yl ester (130052-67-4) + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(91)84047-I

Reference yield: 56.0%

chloramphenicol (56-75-7,85666-84-8) + β-D-galactose peracetate (4163-60-4) → O1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)chloramphenicol + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; for 0.25h;

DOI:10.1081/CAR-120013493

Reference yield: 52.0%

1,3,4,6-tetra-O-acetyl-2-O-trityl-α-D-galactopyranose (130052-61-8) + 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate (135593-74-7) → 1,3,4,6-tetra-O-acetyl-2-O-(2,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl)-α-D-galactopyranose (135617-25-3) + 3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl isothiocyanate + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane; at -5 ℃; for 5.5h;

DOI:10.1016/0008-6215(91)84047-I

upstream raw materials:

β-D-mannose

acetic anhydride

D-Mannose

D-Mannose

Downstream raw materials:

1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside

S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside

1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside

Refernces

• 1、 -. "PROCESS OF SYNTHESIS OF β-6'SULFOQUINOVOSYL DIACYLGLYCEROLS". Page/Page column 11; 12. . Retrieved 2022/02/28.
• 2、 Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan. "Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents". . . Retrieved 2021/12/30.