160549-11-1

Basic information

• Product Name: 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose
• Synonyms: 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose
• CAS NO: 160549-11-1
• Molecular Weight: 434.532
• Mol File: 160549-11-1.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose(160549-11-1)
• EPA Substance Registry System: 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose(160549-11-1)

Safety Data

• Hazardous Substances Data: 160549-11-1(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 67-63-0 isopropyl alcohol 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 100-39-0 benzyl bromide 
• 13265-84-4 D-glucal 
• 89824-86-2 (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran 
• 134502-24-2 2,3,5-tri-O-benzyl-D-arabinitol 1,4-sulfate 
• 134502-23-1 (4R,5S,6R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-[1,3,2]dioxathiepane 2-oxide 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 14233-53-5 3,4,6-tri-O-benzyl-D-arabinitol 
• 74545-14-5 methyl 2-deoxy-3,4,6-tris-O-(phenylmethyl)-α-D-arabino-hexopyranoside 
• 37699-02-8 (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 134502-26-4 (2R,3R,4R)-1,3,4-Tris-benzyloxy-6,6-bis-methylsulfanyl-hexan-2-ol 

Downstream Products

• 132674-50-1 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranose 
• 132674-49-8 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose 
• 220284-26-4 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetamidate 
• 129885-84-3 n-octyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside 
• 129885-84-3 n-octyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside 
• 82252-31-1 cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranoside 
• 82252-30-0 cyclohexyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranoside 
• 256390-59-7 C₄₅H₆₆O₄S 
• 256390-61-1 (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-octadec-(Z)-ylidene-tetrahydro-pyran 
• 256390-60-0 (2R,3S,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-(octadecane-1-sulfonyl)-tetrahydro-pyran 
• 605675-52-3 (2R,3R,4R,6S)-3,4-di(benzyloxy)-2-benzyloxymethyl-1-azabicyclo[4.1.0]heptane 
• 850190-32-8 4,5,7-tri-O-benzyl-2,3,6-trideoxy-2,6-imino-D-manno-heptitol 

Relevant articles and documents

A mild and easy one-pot procedure for the synthesis of 2-deoxysugars from glycals

Glycals can be converted into the corresponding 2-deoxysugars in good yields by treatment with N-iodosuccinimide in CH3CN-H2O 95:5 and removal of the iodide group using Na2S2O4 in DMF/H2O at room temperature. This method is easy to apply, sufficiently mild to allow the survival of acid-sensitive groups such as silyl and trityl ethers and less harmful to the environment than metal-based reactions. (C) 2000 Elsevier Science Ltd.

Mercuration-reductive demercuration of glycals: A mild and convenient entry to 2-deoxy-sugars

Protected glycals, derived from mono-, di- and tri-saccharides, were easily and efficiently converted into the corresponding 2-deoxy-sugars, by reaction with mercuric(II) acetate/sodium borohydride in a polar solvent at 0 °C. The mild and non acidic react

Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors

Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields and regenerate easily separable and reusable phenylpropiolic acid. Deoxy-PPGs containing armed and disarmed groups survived well under the optimized reaction conditions. In addition, the orthogonal nature of D-PPGs was showcased, and 1,1′-linked trehalose-type sugar was also synthesized.

Synthesis of flavonoid 2-deoxyglucosides via the Mitsunobu reaction

The Mitsunobu reaction of flavonoids and 3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose or 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose is a very effective method for the stereoselective synthesis of flavonoid 2-deoxyglucosides. Since there is no C2 substituent

Concise and highly stereoselective syntheses of D-fagomine and 2-epi-fagomine

Highly stereoselective total syntheses of polyhydroxylated piperidines D-fagomine and 2-epi-fagomine have been developed starting from 3,4,6-tri-O-benzyl-D-glucal which is a derivative of D-Glucose. Key steps in the synthesis of these azasugars involved N-Boc-protected amine preparation from oxime followed by stereo specific iodination of alcohol and cascade cyclization triggered by N-Boc deprotection.