2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone
• CAS No.: 13096-62-3
• Molecular Formula: C34H34O6
• Molecular Weight: 538.64
• European Community (EC) Number: 687-263-0
• DSSTox Substance ID: DTXSID20447897
• Nikkaji Number: J370.583H
• Wikidata: Q72504571
• Mol file: 13096-62-3.mol

Synonyms:13096-62-3;2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone;(3R,4S,5R,6R)-3,4,5-TRIS(BENZYLOXY)-6-((BENZYLOXY)METHYL)TETRAHYDRO-2H-PYRAN-2-ONE;(3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one;2,3,4,6-Tetra-O-benzyl-D-gluconic acid-delta-lactone;2,3,4,6-tetra-o-benzyl-d-(+)-glucono-1,5-lactone;MFCD08703228;2,3,4,6-Tetrakis-O-(phenylmethyl)-D-gluconic acid lactone;SCHEMBL500473;DTXSID20447897;AMY40258;AKOS015918438;AC-1439;CS-W005485;AS-19520;T3793;2,3,4,6-tetra-o-benzyl-glucono-1,5-lactone;2-O,3-O,4-O,6-O-Tetrabenzyl-D-gluconic acid lactone;D-Gluconic acid, 2,3,4,6-tetrakis-O-(phenylmethyl)-, delta-lactone;(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxylmethyl)tetrahydro-2H-pyran-2-one;(3r,4s,5r,6r)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydropyran-2-one;(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-one;(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-one (non-preferred name)

Chemical Property of 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.614
• Boiling Point: 677.651 °C at 760 mmHg
• Flash Point: 283.08 °C
• PSA: 63.22000
• Density: 1.22 g/cm³
• LogP: 5.88480
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 538.23553880
• Heavy Atom Count: 40
• Complexity: 705

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC2C(C(C(C(=O)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H]2[C@H]([C@@H]([C@H](C(=O)O2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5
• Uses: 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone is used as a reactant to synthesize various glucoside containing compounds as selective SGLT2 inhibitors for the treatment of type 2 diabetes mellitus.

Technology Process of 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone

There total 33 articles about 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone 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: 100.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3)

Guidance literature:

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide; In dichloromethane; water; at 0 ℃; for 0.333333h; Solvent;

Reference yield: 93.0%

2,3,4,6-tetra-O-benzyl-D-glucopyranoside (59531-24-7) → (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide; at 20 ℃;

DOI:10.1016/j.bmcl.2011.10.062

Reference yield: 88.0%

(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide (128984-82-7) → (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3)

Guidance literature:

Amberlite IR 120 H+; In 1,4-dioxane; for 3h; Heating;

DOI:10.1016/S0040-4039(00)94567-2

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-glucopyranose

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

(2R,3S,4R,5R)-N-benzyl-5-hydroxy-2,3,4,6-tetrabenzyloxyhexanamide

phenacyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

(2,3,4,6-tetra-O-benzyl-1-C-phenyl)-D-glucopyranose

1,2-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-3-chloro-1,2-propanediol

ethyl 2,3,4,6-tetra-O-benzyl-D-gluconate

N-hexyl-2,3,4,6-tetra-O-benzyl-D-gluconamide

Refernces

• 1、 Benhaddou,Czernecki,Farid,Ville,Xie,Zegar. "Tetra-n-propylammonium tetra-oxoruthenate(VII): A reagent of choice for the oxidation of diversely protected glycopyranoses and glycofuranoses to lactones". . p. 243 - 250. Retrieved 1994.
• 2、 -. "Synthesis method of voglibose". Paragraph 0060- 0061; 0075-0077. . Retrieved 2021/08/07.
• 3、 -. "Synthetic method of SGLT2 inhibitor intermediate". Paragraph 0063; 0064. . Retrieved 2021/04/14.