2-(mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate

Base Information

• Chemical Name: 2-(mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate
• CAS No.: 127306-80-3
• Molecular Formula: C₁₈H₂₈N₅O₁₃P
• Molecular Weight: 553.42
• Mol file: 127306-80-3.mol

Synonyms:Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester;

Chemical Property of 2-(mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 278.79000
• Density: g/cm³
• LogP: -2.78574

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-(mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate

There total 6 articles about 2-(mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate 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: 74.0%

Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester (133163-45-8) → 2-(α-D-mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate (127306-80-3)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1021/jm00110a011

Reference yield:

cyanoethyl 2-(2,3,4,6-tetra-O-benzoyl α-D-mannopyranosidyl)ethyl phosphate (127221-61-8) → 2-(α-D-mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate (127306-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triisopropylbenzenesulfonyl-triazole (TPSNT) / pyridine

2: CH₃ONa

With triisopropylbenzenesulfonyl-triazole; sodium methylate; In pyridine;

DOI:10.1016/S0040-4039(01)93843-2

Reference yield:

(2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-(2-benzyloxy-ethoxy)-6-benzyloxymethyl-tetrahydro-pyran (82231-40-1,82231-43-4) → 2-(α-D-mannopyranosidyl)ethyl 3'-azido-3'-deoxy-5'-thymidinyl phosphate (127306-80-3)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd-C

2: 67 percent / CCl₃CN / pyridine / 80 °C

3: triisopropylbenzenesulfonyl-triazole (TPSNT) / pyridine

4: CH₃ONa

With triisopropylbenzenesulfonyl-triazole; hydrogen; sodium methylate; trichloroacetonitrile; palladium on activated charcoal; In pyridine;

DOI:10.1016/S0040-4039(01)93843-2

upstream raw materials:

Phosphoric acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

cyanoethyl 2-(2,3,4,6-tetra-O-benzoyl α-D-mannopyranosidyl)ethyl phosphate

hydroxyethyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

(2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-(2-benzyloxy-ethoxy)-6-benzyloxymethyl-tetrahydro-pyran

Refernces

• 1、 Gouyette,Neumann,Fauve,Huynh-Dinh. "6- And 1- substituted mannosyl phosphotriesters as lipophilic macrophage-targeted carriers of antiviral nucleosides". . p. 6019 - 6022. Retrieved 2007/10/02.