[(2R,3R,4R,5R)-3,4-Dibenzoyloxy-5-isothiocyanatooxolan-2-yl]methyl benzoate

Base Information

• Chemical Name: [(2R,3R,4R,5R)-3,4-Dibenzoyloxy-5-isothiocyanatooxolan-2-yl]methyl benzoate
• CAS No.: 58214-53-2
• Molecular Formula: C27H21NO7S
• Molecular Weight: 503.532
• DSSTox Substance ID: DTXSID30535996
• Nikkaji Number: J1.275.815D
• Mol file: 58214-53-2.mol

Synonyms:58214-53-2;[(2R,3R,4R,5R)-3,4-Dibenzoyloxy-5-isothiocyanatooxolan-2-yl]methyl benzoate;2 3 5-TRI-O-BENZOYL-beta-D-RIBOFURANOSYL;2,3,5-Tri-O-benzoyl-b-D-ribofuranosyl isothiocyanate;DTXSID30535996;2,3,5-Tri-O-benzoyl- beta -D-ribofuranosyl isothiocyanate;2,3,5-Tri-O-benzoyl-beta-D-ribofuranosyl isothiocyanate, >=98.0%;2,3,5-Tri-O-benzoyl-N-(sulfanylidenemethylidene)-beta-D-ribofuranosylamine

Chemical Property of [(2R,3R,4R,5R)-3,4-Dibenzoyloxy-5-isothiocyanatooxolan-2-yl]methyl benzoate

Chemical Property:

• PSA: 132.58000
• LogP: 4.12230
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 503.10387318
• Heavy Atom Count: 36
• Complexity: 811

Purity/Quality:

98% ^*data from raw suppliers

2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl isothiocyanate ≥98.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)N=C=S)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N=C=S)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4

Technology Process of [(2R,3R,4R,5R)-3,4-Dibenzoyloxy-5-isothiocyanatooxolan-2-yl]methyl benzoate

There total 7 articles about [(2R,3R,4R,5R)-3,4-Dibenzoyloxy-5-isothiocyanatooxolan-2-yl]methyl benzoate 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: 80.0%

potassium thioacyanate (333-20-0) + 2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride (5991-01-5) → 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl isothiocyanate (58214-53-2)

Guidance literature:

In acetone; at 20 ℃; for 2h;

DOI:10.1016/S0008-6215(97)00242-5

Reference yield: 74.0%

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide (16205-60-0) → 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl isothiocyanate (58214-53-2)

Guidance literature:

In benzene; at 80 - 90 ℃;

Reference yield:

2,3,5-tri-O-benzoyl-α-D-ribofuranosyl chloride (50909-47-2) + potassium thioacyanate (333-20-0) → 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl isothiocyanate (58214-53-2)

Guidance literature:

With tetrabutylammomium bromide; In acetonitrile; at 82 ℃; for 2h; Molecular sieve;

DOI:10.1055/s-0028-1083156

upstream raw materials:

potassium thioacyanate

2,3,5-(tri-O-benzoyl)-D-ribofuranosyl chloride

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide

2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide

Downstream raw materials:

tri-O-benzoyl-N-[1,2,3,4]thiatriazol-5-yl-β-D-ribofuranosylamine

5,7-dimethyl-3-(tri-O-benzoyl-β-D-ribofuranosylamino)-7H-isothiazolo[3,4-d]pyrimidine-4,6-dione

C₂₈H₂₃N₃O₇S

1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-S-methylisothiobiuret