947747-16-2

Upstream product

• 947747-22-0 C₅₆H₅₇N₃O₈ 
• 956038-72-5 (2S,3S)-3-azido-2-benzyloxy-1-(4-methoxybenzyloxy)-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butane 
• 956038-71-4 (2S,3S)-3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)butane-1,2,4-triol 
• 956038-67-8 (2R,3R)-2,3-O-benzylidene-1-O-(4-methoxybenzyl)butane-1,2,3,4-tetrol 
• 956038-68-9 (2R,3R)-2-O-benzyl-1-O-(4-methoxybenzyl)butane-1,2,3,4-tetrol 
• 956038-69-0 (2R,3R)-3-O-benzyl-4-O-(4-methoxybenzyl)-1-O-(thexyldimethylsilyl)butane-1,2,3,4-tetrol 
• 956038-70-3 (2S,3S)-3-azido-2-O-benzyl-1-O-(4-methoxybenzyl)-4-O-(thexyldimethylsilyl)butane-1,2,4-triol 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 58383-35-0 (R,R)-trans-bis(hydroxymethyl)-1,4-dioxa-5 phenylpentane 
• 947747-20-8 C₄₂H₄₀O₅ 
• 947747-35-5 C₄₃H₄₂O₇S 
• 947747-21-9 C₄₂H₃₉N₃O₄ 
• 947747-17-3 C₂₂H₂₃N₃O₃ 
• 947747-18-4 C₂₂H₂₂O₄ 

Downstream Products

• 947747-43-5 (2S,3S)-3-azido-2-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)butanal 
• 947747-23-1 C₄₇H₅₂N₄O₉ 
• 947747-24-2 C₅₉H₇₁N₃O₈ 
• 947747-45-7 C₅₀H₅₃N₃O₈ 
• 947747-46-8 C₅₀H₅₅N₃O₈ 
• 947747-26-4 C₆₆H₇₉N₃O₈ 
• 947747-47-9 C₅₇H₆₁N₃O₈ 
• 947747-28-6 C₈₁H₁₀₉NO₉ 
• 947747-44-6 C₄₅H₄₇N₃O₉ 
• 383187-82-4 OCH 
• 956038-78-1 (2S,3S,4R)-3-benzyloxy-2-docosanoylamino-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol 
• 956038-77-0 (2S,3S,4R)-3-benzyloxy-2-docosanoylamino-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)octadec-5-yn-4-ol 
• 956038-74-7 (2S,3S,4R)-2-azido-3-benzyloxy-7-phenyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)hept-5-yn-4-ol 
• 956038-73-6 (2S,3S,4R)-2-azido-3-benzyloxy-8-methyl-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyloxy)non-5-yn-4-ol 

Relevant academic research and scientific papers

Concise syntheses of immunostimulating glycolipids, α-galactosyl ceramides

α-Galactosylceramides (α-GalCers) are well known as immunostimulating agents having therapeutic potential. To facilitate the synthesis of α-GalCers and their derivatives, a novel and convergent strategy was designed, which is expected to be versatile for the preparation of a variety of analogues in a diversity-oriented fashion. As an initial demonstration of our strategy, KRN7000 and OCH were synthesized in eight steps from a common intermediate, which is easily obtainable in a multi-gram scale.

A general and stereoselective route to α- or β- galactosphingolipids via a common four-carbon building block

(Chemical Equation Presented) A general synthetic strategy toward α- or β-galactosylceramides and their analogues from 3-azido-2-O-benzyl-1-O- (4-methoxybenzyl)butane-1,2,4-triol is described. The key steps for the installation of the main lipid chain are either a diasteroselective alkynylation reaction yielding the 4R stereocenter of phytosphingosine or a Wittig olefination generating the trans double bond of sphingosine. The methodology allows the preparation of different glycolipids with variations in the structure of the sphingoid base. In particular, three α-GalCer-related compounds have been synthesized and evaluated for their ability to activate CD1d-restricted T-cells.