58341-71-2

Upstream product

• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 35303-86-7 (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 1454799-42-8 O-ethyl-S-[(((methyl 3,4,6-tri-O-benzyl-α-D-glucopyranos-2-yl)dimethylsilyl)methyl)]dithiocarbonate 
• 20672-67-7 (2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol 

Downstream Products

• 88567-45-7 methyl 2-O-benzoyl-4,6-di-O-benzyl-α-D-glucopyranoside 
• 219313-07-2 Methyl 2-O-allyl-4,6-di-O-benzyl-α-[*]-mannopyranoside 
• 215794-92-6 methyl 3-O-allyl-4,6-di-O-benzyl-α-D-glucopyranoside 
• 146195-56-4 methyl 4,6-di-O-benzyl-2-O-p-tolylsulfonyl-α-D-glucopyranoside 
• 405292-06-0 methyl 2-O-acryloyl-4,6-di-O-benzyl-α-D-glucopyranoside 
• 93636-29-4 Acetic acid (2R,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester 
• 93636-30-7 Acetic acid (2R,3R,4R,5S,6R)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester 
• 93636-31-8 Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-5-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-4-yl ester 
• 146195-58-6 methyl 2,3-anhydro-4,6-di-O-benzyl-α-D-mannopyranoside 
• 88567-53-7 methyl 4,6-di-O-benzyl-3-C-methyl-2,3-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosylidene)-α-D-allopyranoside 
• 88567-46-8 methyl 2-O-benzoyl-4,6-di-O-benzyl-α-D-ribo-hexopyranoside-3-ulose 
• 88567-48-0 methyl 4,6-di-O-benzyl-3-C-methyl-2,3-di-O-(trimethylsilyl)-α-D-allopyranoside 
• 88567-47-9 methyl 4,6-di-O-benzyl-3-C-methyl-α-D-allopyranoside 
• 219313-10-7 Benzoic acid (2R,3R,4S,5R,6S)-3-benzyloxy-2-benzyloxymethyl-6-methoxy-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

P-Methylbenzyl Group: Oxidative Removal and Orthogonal Alcohol Deprotection

We describe the practical removal of p-methylbenzyl (MBn) protections of alcohols by treatment with 2,3-dichloro-5,6-dicyano-p-benzoquinone. When a molecule bears benzyl and MBn groups, the oxidant selectively removes the latter groups. Further, the MBn groups tolerate ceric ammonium nitrate, resulting in chemoselective removal of the p-methoxybenzyl group in the presence of the MBn groups. These orthogonal alcohol deprotections would provide novel synthetic strategies of organic compounds.

A tin-free regioselective radical de-o-benzylation by an intramolecular hydrogen atom transfer on carbohydrate templates

Radically selective: A remarkable 1,7-hydrogen atom transfer of a benzylic hydrogen atom to an O-silylmethylene radical initiates a regioselective de-O-benzylation of benzylated saccharides. The reaction terminates by an ionic mechanism and is general for hydroxy benzylated substrates having a variety of functional groups. Copyright

A new method for the deprotection of benzyl ethers or the selective protection of alcohols

A new selective method for the deprotection of benzyl ethers situated next to alcohols in the α, β, or γ position is presented which uses either NIS or DIB/I2 as a reagent. After initial formation of a hypoiodite intermediate, the reaction is b

A new intramolecular reaction for the regioselective debenzylation or protection of alcohols

Strained benzylidene acetals such as 1 can be prepared with a new intramolecular reaction that allows the selective removal of benzyl protecting groups neighboring free OH groups, without attacking other benzyl groups. The mechanism of this reaction, which is useful for carbohydrate synthesis, probably proceeds via ionic intermediates with neighboring group participation.

REGIOSELECTIVE ALKYLATION via TRIALKYLSTANNYLATION: METHYL α-D-GLUCOPYRANOSIDE

Partial stannylation of methyl α-D-glucopyranoside with (Bu3Sn)2O, and subsequent alkylation with benzyl bromide, allyl bromide, and trityl chloride, afforded the 2,6-disubstituted derivative as one of major products in each case.