(3R,4S,5R)-4-Formyloxy-3-iodomethyl-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)-4-Formyloxy-3-iodomethyl-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester
CAS No.:220567-95-3
Molecular Formula:C₂₅H₃₇IO₈
Molecular Weight:592.468
Hs Code.:

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

There total 9 articles about (3R,4S,5R)-4-Formyloxy-3-iodomethyl-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: 55.0%

: 220567-91-9
{(2S,3R)-5-Hydroxy-2-[(R)-(4-methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

: 220567-95-3
(3R,4S,5R)-4-Formyloxy-3-iodomethyl-5-(4-methoxy-benzyloxy)-5-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-pentanoic acid tert-butyl ester

Guidance literature:: With [bis(acetoxy)iodo]benzene; iodine; In cyclohexane; for 1h; Irradiation;
DOI:10.1016/S0040-4020(98)01206-X

Reference yield:

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

: 220567-95-3
(3R,4S,5R)-4-Formyloxy-3-iodomethyl-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 3 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

With [bis(acetoxy)iodo]benzene; iodine; diisobutylaluminium hydride; lithium diisopropyl amide; In 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

: 220567-95-3
(3R,4S,5R)-4-Formyloxy-3-iodomethyl-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 6 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

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