(2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate

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Chemical Name:(2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate
CAS No.:1611470-13-3
Molecular Formula:C₆₂H₆₀O₁₁
Molecular Weight:981.152
Hs Code.:

Synonyms:(2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate

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Chemical Property of (2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate

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Technology Process of (2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate

There total 8 articles about (2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl 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: 95.0%

: 5443-10-7
1,3-bis (trityloxy)propan-2-ol

: 1374633-04-1
(2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate

: 1611470-13-3
(2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate

Guidance literature:: 1,3-bis (trityloxy)propan-2-ol; (2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate; With N-iodo-succinimide; In dichloromethane; at 0 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 4h; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.tet.2014.04.069

Reference yield:

: 920267-56-7
4-methylphenyl 1-thio-β-D-galactofuranoside

: 1611470-13-3
(2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: (1S)-10-camphorsulfonic acid / dichloromethane / 2 h / 20 °C

2.1: 1H-imidazole; dmap / dichloromethane / 0 - 20 °C

3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

5.1: pyridine / 2 h / 0 - 20 °C

6.1: N-iodo-succinimide / dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

6.2: 4 h / 0 °C / Molecular sieve; Inert atmosphere

With pyridine; 1H-imidazole; dmap; N-iodo-succinimide; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2014.04.069

Reference yield:

: 1374632-99-1
(2R,3S,4R,5S)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(p-tolylthio)tetrahydrofuran-3-ol

: 1611470-13-3
(2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 3 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

3.1: pyridine / 2 h / 0 - 20 °C

4.1: N-iodo-succinimide / dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

4.2: 4 h / 0 °C / Molecular sieve; Inert atmosphere

With pyridine; dmap; N-iodo-succinimide; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2014.04.069