1,2-O-Isopropylidene-5-O-triphenylmethyl-alpha-D-xylofuranoside

Base Information

• Chemical Name: 1,2-O-Isopropylidene-5-O-triphenylmethyl-alpha-D-xylofuranoside
• CAS No.: 20590-53-8
• Molecular Formula: C27H28O5
• Molecular Weight: 432.516
• DSSTox Substance ID: DTXSID401169287
• Nikkaji Number: J1.269.239K
• Mol file: 20590-53-8.mol

Synonyms:20590-53-8;1,2-O-ISOPROPYLIDENE-5-O-TRIPHENYLMETHYL-ALPHA-D-XYLOFURANOSIDE;(3aR,5R,6S,6aR)-2,2-dimethyl-5-(trityloxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol;1,2-o-(1-methylethylidene)-5-o-(triphenylmethyl)-alpha-d-xylofuranose;SCHEMBL3276211;DTXSID401169287;1,2-Di-O-methyl-myo-mositol;Viscumitol;A900462;1-O,2-O-Isopropylidene-5-O-trityl-alpha-D-xylofuranose

Chemical Property of 1,2-O-Isopropylidene-5-O-triphenylmethyl-alpha-D-xylofuranoside

Chemical Property:

• PSA: 57.15000
• LogP: 4.23240
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 432.19367399
• Heavy Atom Count: 32
• Complexity: 558

Purity/Quality:

97% ^*data from raw suppliers

1,2-O-ISOPROPYLIDENE-5-O-TRIPHENYLMETHYL-ALPHA-D-XYLOFURANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)O)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)COC(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)O)C

Technology Process of 1,2-O-Isopropylidene-5-O-triphenylmethyl-alpha-D-xylofuranoside

There total 13 articles about 1,2-O-Isopropylidene-5-O-triphenylmethyl-alpha-D-xylofuranoside 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: 100.0%

trityl chloride (76-83-5) + 1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1002/chem.200700141

Reference yield: 94.0%

3-O-chloroacetyl-1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (1352550-60-7) → 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2011.09.033

Reference yield: 92.0%

(((4-methoxybenzyl)oxy)methanetriyl)tribenzene (312493-51-9) + 1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8)

Guidance literature:

With 4 A molecular sieve; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 0.166667h;

upstream raw materials:

trityl chloride

1,2-O-isopropylidene-α-D-xylose

(((4-methoxybenzyl)oxy)methanetriyl)tribenzene

(((3-methylbut-2-en-1-yl)oxy)methanetrityl)tribenzene

Downstream raw materials:

O¹,O²-isopropylidene-O³-methyl-O⁵-trityl-α-D-xylofuranose

1,2-O-isopropylidene-3-(2-methoxy-ethoxy)-5-O-trityl-D-xylofuranose

5-O-trityl-3-O-ethyl-1,2-isopropylidene-α-D-xylopyranoside

5-O-trityl-3-O-propyl-1,2-isopropylidene-α-D-xylopyranoside

Refernces

• 1、 -. "ANTIBODY-STING AGONIST CONJUGATES AND THEIR USE IN IMMUNOTHERAPY". Paragraph 00284; 00286. . Retrieved 2021/01/29.
• 2、 Ler, Geraldine J. M.,Xu, Weijun,Mak, Jeffrey Y. W.,Liu, Ligong,Bernhardt, Paul V.,Fairlie, David P.. "Computer Modelling and Synthesis of Deoxy and Monohydroxy Analogues of a Ribitylaminouracil Bacterial Metabolite that Potently Activates Human T Cells". . p. 15594 - 15608. Retrieved 2019/11/16.