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
• General Description: 2,3,4,6-Tetra-O-benzyl-D-glucono-1,5-lactone is a protected sugar derivative used as a key intermediate in carbohydrate chemistry, particularly in the synthesis of glycopyranosylidene 1,1-diazides. It serves as a precursor for reactions under phase-transfer catalysis (PTC) conditions, offering improved efficiency and yield compared to alternative methods. Its reactivity is notable in the synthesis of D-gluco diazides, where it demonstrates higher reactivity than analogous D-galacto or D-manno derivatives.

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:

5-(D_r-1c_F,2t_F,3c_F,5-tetrakis-benzyloxy-4r_F-hydroxy-pent-cat_F-yl)-oxazole-4-carboxylic acid ethyl ester

5-(D_r-1c_F,2t_F,3c_F,5-tetrakis-benzyloxy-4r_F-hydroxy-pent-cat_F-yl)-oxazole-4-carboxylic acid benzyl ester

2,3,4,6-Tetra-O-benzyl-N,N-dimethyl-D-gluconamid

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

Refernces

Synthesis of protected glycopyranosylidene 1,1-diazides

10.1055/s-1996-4264

This research outlines the synthesis of protected glycopyranosylidene 1,1-diazides, which are important intermediates in carbohydrate chemistry. The study aimed to develop efficient, safe, and improved methods for preparing these compounds from acetylated sugar dihalides or tetrabenzyl D-glucono-1,5-lactone. The researchers concluded that the use of phase-transfer catalysis (PTC) conditions was more effective than using sodium azide in DMSO for halogen substitution, leading to fair to excellent yields of D-gluco and D-galacto diazides. They also found that the reactivity of the substrates decreased in the order D-gluco > D-galacto > D-manno.