108739-68-0

Basic information

• Product Name: methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• Synonyms: methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• CAS NO: 108739-68-0
• Molecular Weight: 987.199
• Mol File: 108739-68-0.mol
• Article Data: 222

Chemical Properties

• CAS DataBase Reference: methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside(108739-68-0)
• EPA Substance Registry System: methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside(108739-68-0)

Safety Data

• Hazardous Substances Data: 108739-68-0(Hazardous Substances Data)

Upstream product

• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 96863-21-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 3019-71-4 Trichloroacetyl isocyanate 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 113533-73-6 (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran 
• 70893-32-2 2-benzothiazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 78687-40-8 methyl 2,3,4-tri-O-benzyl-6-O-(trimethylsilyl)-α-D-glucopyranoside 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 

Downstream Products

• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 

Relevant articles and documents

Reagent Controlled Stereoselective Synthesis of α-Glucans

The development of a general glycosylation method that allows for the stereoselective construction of glycosidic linkages is a tremendous challenge. Because of the differences in steric and electronic properties of the building blocks used, the outcome of

Stereodivergent Mannosylation Using 2- O-(ortho-Tosylamido)benzyl Group

We report a novel strategy for obtaining both anomers from a single mannosyl donor equipped with a C2-o-TsNHbenzyl ether (2-O-TAB) by switching reaction conditions. In particular, the formation of various β-mannosides was achieved with high selectivity by using a mannosyl phosphite in the presence of ZnI2.

Novel dehydrative glycosylation by using acid anhydride and TMSClO4

Novel dehydrative glycosylation with 1-hydroxy sugars as glycosyl donors was achieved. Combination of trifluoroacetic anhydride or trichloroacetic anhydride as dehydrating agents with TMSClO4 as a Lewis acid afforded desired glycosides in good

A New Glycosylation Procedure Utilizing Rare Earth Salts and Glycosyl Fluorides, with or without the Requirement of Lewis Acids

-

One-pot preparation and activation of glycosyl trichloroacetimidates: Operationally simple glycosylation induced by combined use of solid-supported, reactivity-opposing reagents

By the combined use of solid-supported reactivity-opposing reagents, that is, basic PTBD and acidic Nafion-SAC resins, sequential reactions consisting of glycosyl trichloroacetimidate formation and glycosylation can be effected in a one-pot ope

A stereoselective glycosidation using thioglycosides, activation by combination of N-bromosuccinimide and strong acid salts

A stereoselective glycosidation with thioglycosides was effected under mild and neutral conditions by combined use of N-bromosuccinimide (NBS) and a catalytic amount of various strong acid salts. A combination of NBS with Ph2IOTf, Bu4NOTf, or Bu4NClO4 was advantageous for β-selective glucosidation with 2-O-acylated or 2-O-benzylated donors by virtue of either the neighboring group participation or the known solvent effect of nitrile, respectively. α-Selective glucosidation was effected by the use of a 2-O-benzylated donor in the presence of LiClO4 or LiNO3 as a catalyst in ether. Addition of silica gel to the reaction mixture increased both the α-selectivity and reaction rate.

A catalytic and stereoselective glycosylation with glucopyranosyl fluoride by using various protic acids

A catalytic and stereoselective glycosylation with glucosyl fluoride was effectively performed by using a catalytic amount of various protic acids. When the glycosylation was carried out, for example, using perchloric acid (HClO4) in diethyl et

Activation of glycosyl phosphates by in situ conversion to glycosyl iodides under neutral conditions in concentrated solutions of lithium perchlorate in organic solvents

Glycosyl phosphates are converted in situ into glycosyl iodides and thereby advantageously employed as glycosyl donors under mild neutral conditions by treatment with LiI in IM solutions of LiClO4 in organic solvents.

Efficient Synthesis of α-Glycosyl Chlorides Using 2-Chloro-1,3-dimethylimidazolinium Chloride: A Convenient Protocol for Quick One-Pot Glycosylation

A mild and convenient method for the synthesis of α-glycosyl chlorides in high 80–96 % yields within 15–30 min using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) is disclosed. The method has a wide substrate scope and is compatible with labile OH protecting groups, including benzyl, acetyl, benzoyl, isopropylidene, benzylidene, TBDMS (tert-butyldimethylsilyl), and TBDPS (tert-butyldiphenylsilyl) groups. The excellent α selectivity obtained in this reaction is attributed to in-situ isomerization of β-glycosyl chlorides to the more stable α-glycosyl chlorides, as demonstrated by 1H NMR spectroscopic studies. Disarmed sugars with OBz or OAc groups at C-2 were chlorinated at a faster rate but ismomerized (β→α) at a slower rate than armed sugars with an OBn group at C-2. More importantly, the method enables highly desirable one-pot glycosylation reactions to take place, thus allowing efficient syntheses of disaccharides and simple O-glycosylated sugars in high overall yields without the need for separation or purification of the α-glycosyl chloride donors. This method will be especially useful for direct glycosylation reactions using glycosyl chloride donors that are unstable upon separation and purification.

BF3·OEt2 enhanced Yb(OTf)3-promoted glycosidation of 1-O-acyl-D-glucopyranose 1

-

Catalytic and stereoselective glycosylation with glucosyl thioformimidates

A novel and efficient glycosyl donor having a p- trifluoromethylbenzylthio-N-p-trifluoromethylphenylformimidate group at an anomeric position is easily prepared by the addition of anomeric hydroxy group of 2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranose to p-t

A new glycosylation method using glycosyl donors substituted by enol ether as a leaving group

Glycosyl donors having a leaving group of enol ether were easily prepared by the addition of the anomeric hydroxyl group of pyranose derivatives to α,β-unsaturated alkynic acid esters or -ketone. These glycosyl donors were selectively glycosidated with se

Contrasting reactivity of thioglucoside and selenoglucoside donors towards promoters: implications for glycosylation stereocontrol

The stereochemical outcome of glycosylation reactions with model thioglycosides and selenoglycosides proved to be dependent on the source of promoter iodonium ion, with iodine giving different results to N-iodosuccinimide (NIS) alone or N-iodosuccinimide/

A novel method for stereoselective glycosidation with thioglycosides: Promotion by hypervalent iodine reagents prepared from PhIO and various acids

Combinations of iodosobenzene (PhIO) and various acids effectively promoted glycosidation using thioglycosides as glycosyl donors. β-Selective glucosidation was effected by use of TfOH, Tf2O, TMSOTf, Sn(OTf)2, and Yb(OTf)3 as catalysts with 2-O-benzoylated or 2-O-benzylated donors by virtue of either the neighboring group participation or the solvent effect of acetonitrile, respectively. Combinations of PhIO with SnCl2-AgClO4-AgClO4, BiCl3-AgClO4, and SbCl3-AgClO4 in ether were advantageous for α-glucosidation, where 2,2,2-trichloroethoxycarbonyl group introduced at the 6-position of a 2-O-benzylated donor remarkably increased α-sensitivity.

Gallium reagents in organic synthesis: Dimethylgallium chloride and triflate as activators in glycosidation using glycopyranosyl fluorides

Gallium compounds were utilized in organic synthesis for the first time. Dimethylgallium chloride and dimethylgallium triflate was found to efficiently promote the glycosidation using several glycopyranosyl fluorides.

O-glycoside synthesis with glycosyl iodides under neutral conditions in 1 M LiClO4 in CH2Cl2

Glycosyl phosphates, imidates, trifluoroacetates, chlorides, and bromides are converted into the respective glycosyl iodides by treatment with LiI or NaI in 1 M solutions of LiClO4 in CH2Cl2. Under these neutral conditions

Novel α-mannoside synthesis promoted by the combination of trimethylsilyl chloride and zinc triflate

α-Mannosides were obtained in good yields and with good selectivity directly from benzyl-protected mannopyranosyl p-nitrobenzoate or acetate using a trimethylsilyl chloride-zinc triflate catalyst system.

Aryl(trifluoroethyl)iodonium Triflimide and Nitrile Solvent Systems: A? Combination for the Stereoselective Synthesis of Armed 1,2-trans-β-Glycosides at Noncryogenic Temperatures

Armed thioglycosides can be activated with aryl(trifluoroethyl)iodonium triflimide in 2:1 CH2Cl2/pivalonitrile or a solvent combination of CH2Cl2, acetonitrile, isobutyronitrile, and pivalonitrile (6:1:1:1) at 0

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2- Cis-Selective Glucosylation of Reactive Alcohols

Here, we demonstrate that substitution of the benzyl groups of glucosyl imidate donors with trifluoromethyl results in a substantial increase in 1,2-cis-selectivity when activated with TMS-I in the presence of triphenylphosphine oxide. Stereoselectivity is dependent on the number of trifluoromethyl groups (4-trifluoromethylbenzyl vs 3,5-bis-trifluoromethylbenzyl). Particularly encouraging is that we observe high 1,2-cis-selectivity with reactive alcohol acceptors.