10230-17-8

Basic information

• Product Name: 3-O-BENZYL-D-GLUCOPYRANOSE
• Synonyms: 3-O-BENZYL-BETA-D-GLUCOSE;3-O-BENZYL-D-GLUCOPYRANOSE;3-O-Benzyl-β-D-Glucose;3-O-Benzyl-D-glucopyranose min. 99%;D-Glucose, 3-O-(phenylmethyl)-
• CAS NO: 10230-17-8
• Molecular Formula: C₁₃H₁₈O₆
• Molecular Weight: 270.28
• Product Categories: Sugars, Carbohydrates & Glucosides
• Mol File: 10230-17-8.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 493.386 °C at 760 mmHg
• Flash Point: 252.191 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 3-O-BENZYL-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-BENZYL-D-GLUCOPYRANOSE(10230-17-8)
• EPA Substance Registry System: 3-O-BENZYL-D-GLUCOPYRANOSE(10230-17-8)

Safety Data

• Hazardous Substances Data: 10230-17-8(Hazardous Substances Data)

Usage

General Description

3-O-Benzyl-D-glucopyranose is a chemical compound with the molecular formula C18H22O6. It is a derivative of D-glucose in which a benzyl group is attached to the third carbon atom of the glucose ring. 3-O-BENZYL-D-GLUCOPYRANOSE has a white solid appearance and is commonly used in organic synthesis and pharmaceutical research. It is a key intermediate for the synthesis of various carbohydrate-based molecules and is also utilized in the preparation of glycoside derivatives. 3-O-Benzyl-D-glucopyranose is known for its potential applications in the development of new drugs and active pharmaceutical ingredients.

InChI:InChI=1/C13H18O6/c14-6-9-10(15)12(11(16)13(17)19-9)18-7-8-4-2-1-3-5-8/h1-5,9-17H,6-7H2/t9-,10-,11-,12+,13-/m1/s1

Synthetic route

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → O3-benzyl-D-glucose (10230-17-8)

Conditions	Yield
With sulfuric acid
With sulfuric acid
With hydrogenchloride
(acid hydrolysis);

O3-benzyl-O1,O2-benzylidene-O5,O6-isopropylidene-D-glucose → O3-benzyl-D-glucose (10230-17-8)

Conditions	Yield
With sulfuric acid

benzyl chloride (100-44-7) → O3-benzyl-D-glucose (10230-17-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide 2: aqueous methanol. HCl View Scheme

benzyl bromide (100-39-0) + sodium compound of cyclohexanol → O3-benzyl-D-glucose (10230-17-8)

Conditions	Yield
Multi-step reaction with 2 steps 2: aqueous methanol. H2SO4 View Scheme

methanol (67-56-1) + O3-benzyl-D-glucose (10230-17-8) → methyl-(O3-benzyl-O2,O4,O6-trimethyl-ξ-D-glucopyranoside) (39708-09-3, 39708-10-6, 69412-16-4)

Conditions	Yield
With hydrogenchloride Behandeln mit Methyljodid unter Zusatz von Silberoxid;

methanol (67-56-1) + O3-benzyl-D-glucose (10230-17-8) → methyl 3-O-benzyl-α,β-D-glucopyranoside (108644-64-0)

Conditions	Yield
With hydrogenchloride

O3-benzyl-D-glucose (10230-17-8) → O2-Benzyl-arabinose (884484-13-3)

Conditions	Yield
With sodium periodate Behandeln des Reaktionsprodukts mit einem Kationen-Austauscher in H2O bei 100grad; O2-benzyl-D-arabinose;
With sodium periodate Behandeln des Reaktionsprodukts mit wss. NaOH; O2-benzyl-D-arabinose;

O3-benzyl-D-glucose (10230-17-8) → O3-benzyl-D-glucose-p-tolylimine

O3-benzyl-D-glucose (10230-17-8) + acetic anhydride (108-24-7) → 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (39686-94-7, 56632-47-4, 65827-58-9, 99202-62-7, 99202-66-1, 103082-79-7, 103703-00-0, 103703-01-1, 118711-49-2, 127853-23-0, 139563-66-9)

Conditions	Yield
With pyridine

O3-benzyl-D-glucose (10230-17-8) + trityl chloride (76-83-5) → O3-Benzyl-O6-trityl-D-glucose (139521-79-2)

Conditions	Yield
With pyridine

O3-benzyl-D-glucose (10230-17-8) + trityl chloride (76-83-5) → O1,O2,O4-Triacetyl-O3-benzyl-O6-trityl-ξ-D-glucopyranose (66963-59-5)

Conditions	Yield
With pyridine Behandeln mit Acetanhydrid und Pyridin;

O3-benzyl-D-glucose (10230-17-8) + benzoyl chloride (98-88-4) → 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-D-glucopyranoside (30572-04-4)

Conditions	Yield
With pyridine

O3-benzyl-D-glucose (10230-17-8) + phenylhydrazine (100-63-0) → O3-benzyl-D-arabino-[2]hexosulose-bis-phenylhydrazone (118020-54-5)

4-phenylazobenzoyl chloride (104-24-5) + O3-benzyl-D-glucose (10230-17-8) → O3-Benzyl-O1,O2,O4,O6-tetrakis-(4-phenylazo-benzoyl)-ξ-D-glucopyranose

Conditions	Yield
With pyridine

O3-benzyl-D-glucose (10230-17-8) + methyl iodide (74-88-4) → methyl-(O3-benzyl-O2,O4,O6-trimethyl-ξ-D-glucopyranoside) (39708-09-3, 39708-10-6, 69412-16-4)

Conditions	Yield
With silver(l) oxide

O3-benzyl-D-glucose (10230-17-8) → 2-deoxy-D-ribonic acid (7284-15-3)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

O3-benzyl-D-glucose (10230-17-8) → 3-deoxyglucosone (4134-97-8, 30382-30-0, 50455-94-2, 82399-12-0, 4084-27-9)

Conditions	Yield
With sodium hydroxide

O3-benzyl-D-glucose (10230-17-8) + aqueous Ca(OH)2 + oxygen → D-arabino-3-deoxy-hexonic acid (1518-59-8) + calcium salts of/the/ D-ribo-3-deoxy-hexonic acid

Conditions	Yield
at 25℃; Rate constant;

Upstream product

• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 139521-79-2 O³-Benzyl-O⁶-trityl-D-glucose 
• 1518-59-8 D-arabino-3-deoxy-hexonic acid 
• 7284-15-3 2-deoxy-D-ribonic acid 
• 39708-09-3 methyl-(O³-benzyl-O²,O⁴,O⁶-trimethyl-ξ-D-glucopyranoside) 
• 118020-54-5 O³-benzyl-D-arabino-[2]hexosulose-bis-phenylhydrazone 
• 30572-04-4 1,2,4,6-tetra-O-benzoyl-3-O-benzyl-β-D-glucopyranoside 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 108644-64-0 methyl 3-O-benzyl-α,β-D-glucopyranoside