(3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

Base Information

Chemical Name:(3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester
CAS No.:220568-02-5
Molecular Formula:C₂₅H₃₉IO₇
Molecular Weight:578.485
Hs Code.:

Synonyms:(3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

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Chemical Property of (3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

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Technology Process of (3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

There total 11 articles about (3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl 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: 89.0%

: 420-37-1
trimethoxonium tetrafluoroborate

: 220568-00-3
(3R,4S,5R)-4-Hydroxy-3-iodomethyl-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

: 220568-02-5
(3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

Guidance literature:: With Proton Sponge; In tetrahydrofuran; for 17h; Ambient temperature;
DOI:10.1016/S0040-4020(98)01206-X

Reference yield:

: 540-88-5
acetic acid tert-butyl ester

: 220568-02-5
(3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 15 min

2: 50 percent / DIBAL / diethyl ether; hexane / 1.75 h / -78 °C

3: 55 percent / PhI(OAc)2, I₂ / cyclohexane / 1 h / Irradiation

4: 100 percent / aq. KHCO₃ / methanol / 5 h / Ambient temperature

5: 89 percent / Proton Sponge / tetrahydrofuran / 17 h / Ambient temperature

With Proton Sponge; [bis(acetoxy)iodo]benzene; iodine; diisobutylaluminium hydride; potassium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; cyclohexane;
DOI:10.1016/S0040-4020(98)01206-X

Reference yield:

: 99603-55-1
(4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde

: 220568-02-5
(3R,4S,5R)-3-Iodomethyl-4-methoxy-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 71 percent / SnCl₄ / CH₂Cl₂ / 15 h / -78 °C

2: 80 percent / HF*pyridine / pyridine / 0.17 h / 0 °C

3: 75 percent / (+/-)-camphor sulfonic acid / CH₂Cl₂ / 69 h / Ambient temperature

4: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 15 min

5: 50 percent / DIBAL / diethyl ether; hexane / 1.75 h / -78 °C

6: 55 percent / PhI(OAc)2, I₂ / cyclohexane / 1 h / Irradiation

7: 100 percent / aq. KHCO₃ / methanol / 5 h / Ambient temperature

8: 89 percent / Proton Sponge / tetrahydrofuran / 17 h / Ambient temperature

With Proton Sponge; [bis(acetoxy)iodo]benzene; (+/-)-camphor sulfonic acid; iodine; tin(IV) chloride; diisobutylaluminium hydride; potassium hydrogencarbonate; pyridine hydrogenfluoride; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; cyclohexane;
DOI:10.1016/S0040-4020(98)01206-X