6-O-Trityl-1,2,3,4-tetra-O-benzyl-β-D-glucopyranose

Base Information

• Chemical Name: 6-O-Trityl-1,2,3,4-tetra-O-benzyl-β-D-glucopyranose
• CAS No.: 27851-28-1
• Molecular Formula: C53H50 O6
• Molecular Weight: 782.976
• Mol file: 27851-28-1.mol

Synonyms:Glucopyranoside,benzyl 2,3,4-tri-O-benzyl-6-O-trityl-, b-D- (8CI); Benzyl 2,3,4-tri-O-benzyl-6-O-trityl-b-D-glucopyranoside

Chemical Property of 6-O-Trityl-1,2,3,4-tetra-O-benzyl-β-D-glucopyranose

Chemical Property:

• PSA: 55.38000
• LogP: 10.69300

Purity/Quality:

97% ^*data from raw suppliers

1,2,3,4-Tetra-O-benzyl-6-O-trityl-b-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-O-Trityl-1,2,3,4-tetra-O-benzyl-β-D-glucopyranose

There total 12 articles about 6-O-Trityl-1,2,3,4-tetra-O-benzyl-β-D-glucopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol (39687-20-2) + benzyl bromide (100-39-0) → (2R,3R,4S,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran (27851-28-1,39687-22-4)

Guidance literature:

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; Further stages.;

DOI:10.1039/b212066f

Reference yield:

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (4304-12-5) → (2R,3R,4S,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran (27851-28-1,39687-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 78 percent / DMAP / pyridine / 7 h / 60 °C

2.1: NaH / dimethylformamide / 0.17 h / 0 °C

2.2: 82 percent / dimethylformamide / 20 °C

With dmap; sodium hydride; In pyridine; N,N-dimethyl-formamide;

DOI:10.1039/b212066f

Reference yield:

benzyl bromide (100-39-0) + 6-O-trityl-D-glucopyranose (54325-28-9) → benzyl 6-O-trityl-2,3,4-tri-O-benzyl-D-glucopyranoside (39687-22-4) + (2R,3R,4S,5R,6R)-2,3,4,5-tetrakis(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran (27851-28-1,39687-22-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; Title compound not separated from byproducts.;

DOI:10.1016/j.tet.2007.07.027

upstream raw materials:

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-((trityloxy)methyl)tetrahydro-2H-pyran-3,4,5-triol

benzyl bromide

6-O-trityl-D-glucopyranose

D-Glucose

Downstream raw materials:

(2S,3S,4S,5R,6R)-3,4,5,6-tetrakis(benzyloxy)tetrahydro-2H-pyran-2-carboxylic acid

benzyl 2,3,4-tri-O-benzyl-6-O-(N-(2-ethyl-2,8-diazaspiro[4,5]decane-1,3-dione)aminocarbonyl)-β-D-glucopyranoside

5-acetoxy-3-(6-acetoxymethyl-3-azido-4-benzyloxy-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-(3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

3-(3-azido-4-benzyloxy-6-hydroxymethyl-5-methoxy-tetrahydro-pyran-2-yloxy)-4-benzyloxy-5-hydroxy-6-(3,4,5,6-tetrakis-benzyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Refernces

• 1、 Kaji, Eisuke,Komori, Teruaki,Yokoyama, Masaki,Kato, Tomomi,Nishino, Takashi,Shirahata, Tatsuya. "Efficient synthesis of the functional central core lactides, a constituent of antibiotic fattiviracins". experimental part. p. 4089 - 4100. Retrieved 2010/07/08.
• 2、 Amigues,Greenberg,Ju,Chen,Migaud. "Synthesis of cyclophospho-glucoses and glucitols". . p. 10042 - 10053. Retrieved 2008/02/13.