(2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

Base Information

Chemical Name:(2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate
CAS No.:1583259-33-9
Molecular Formula:C₄₀H₅₇NO₆Si
Molecular Weight:675.981
Hs Code.:

Synonyms:(2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

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Chemical Property of (2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

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Technology Process of (2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

There total 6 articles about (2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate 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: 82.0%

: 1583259-18-0
(Z)-5-isopropoxy-2,2,3,3,9,9-hexamethyl-8,8-diphenyl-4,7-dioxa-3,8-disiladec-5-ene

: 1583259-07-7
(R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal

: 1583259-33-9
(2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

Guidance literature:: With titanium(IV) dichlorodiisopropylate; In dichloromethane; at -20 ℃; for 16h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ja502205q

Reference yield:

: 19790-60-4
3-Benzyloxypropanal

: 1583259-33-9
(2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1: copper dichloride; CHF₃O₃S*C₁₃H₁₈N₂O / diethyl ether / 48 h / -30 °C / Molecular sieve; Inert atmosphere

2: titanium(IV) dichlorodiisopropylate / dichloromethane / 16 h / -20 °C / Inert atmosphere

With titanium(IV) dichlorodiisopropylate; CHF₃O₃S*C₁₃H₁₈N₂O; copper dichloride; In diethyl ether; dichloromethane; 2: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q

Reference yield:

: 100-39-0
benzyl bromide

: 1583259-33-9
(2R,3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-2-((tert-butyldiphenylsilyl)oxy)-4-(2,2,6,6-tetramethylpiperidin-1-yloxy)pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 16 h / 20 °C

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C

3.1: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve

4.1: titanium(IV) dichlorodiisopropylate / dichloromethane / 16 h / -20 °C / Inert atmosphere

With titanium(IV) dichlorodiisopropylate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; sodium hydride; copper dichloride; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; mineral oil; 4.1: |Mukaiyama Aldol Addition;
DOI:10.1021/ja502205q