(αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester

Base Information

Chemical Name:(αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester
CAS No.:1452798-35-4
Molecular Formula:C₃₀H₄₂N₆O₁₃Si
Molecular Weight:725.758
Hs Code.:

(αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester

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Chemical Property of (αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester

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Technology Process of (αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester

There total 9 articles about (αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester 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: 63.0%

: 1452798-28-5
(2S,3R)-2-methyloxycarbonylamino-3-trimethylsilylhydroxy-4-iodobutyric acid methyl ester

: 1452798-32-1
4-methyl-6-([D₃]-methyl)-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]-purin-9-one

: 1452798-35-4
(αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester

Guidance literature:: 4-methyl-6-([D₃]-methyl)-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]-purin-9-one; With 2-methylpropylmagnesium chloride; In tetrahydrofuran; at -78 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

(2S,3R)-2-methyloxycarbonylamino-3-trimethylsilylhydroxy-4-iodobutyric acid methyl ester; With copper(I) cyanide di(lithium chloride); In tetrahydrofuran; at -78 - -25 ℃; for 16h; Schlenk technique; Inert atmosphere;
DOI:10.1002/chem.201204209

Reference yield:

: 1452798-23-0
(2S)-2-carboxymethylamino-4-bromo-butyric acid methyl ester

: 1452798-35-4
(αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium tetrahydroborate / methanol / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: pyridine; dihydrogen peroxide / tetrahydrofuran / 1.5 h / Reflux

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 96 h / 20 °C / Inert atmosphere

4.1: magnesium iodide / diethyl ether; toluene / 1.5 h / -50 °C / Inert atmosphere

5.1: pyridine / dichloromethane / 43 h / 20 °C / Inert atmosphere

6.1: 2-methylpropylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere

6.2: 16 h / -78 - -25 °C / Schlenk technique; Inert atmosphere

With pyridine; sodium tetrahydroborate; 2-methylpropylmagnesium chloride; dihydrogen peroxide; 3-chloro-benzenecarboperoxoic acid; magnesium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1002/chem.201204209

Reference yield:

: 119484-07-0
(2S)-2-methyloxycarbonylaminovinylglycine-O-methyl ester

: 1452798-35-4
(αS,βS)-α-[(methoxycarbonyl)amino]-β-(trimethylsilyloxy)-4-methyl-6-[2H3]-methyl-9-oxo-3-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-4,9-dihydro-3H-imidazo[1,2-α]purine-7-butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 96 h / 20 °C / Inert atmosphere

2.1: magnesium iodide / diethyl ether; toluene / 1.5 h / -50 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 43 h / 20 °C / Inert atmosphere

4.1: 2-methylpropylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 °C / Schlenk technique; Inert atmosphere

4.2: 16 h / -78 - -25 °C / Schlenk technique; Inert atmosphere

With pyridine; 2-methylpropylmagnesium chloride; 3-chloro-benzenecarboperoxoic acid; magnesium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1002/chem.201204209