{(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

Base Information

• Chemical Name: {(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
• CAS No.: 220567-91-9
• Molecular Formula: C₂₅H₃₈O₈
• Molecular Weight: 466.572
• Mol file: 220567-91-9.mol

Synonyms:{(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

Chemical Property of {(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(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

There total 8 articles about {(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 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: 50.0%

{(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester (220567-88-4) → {(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 (220567-91-9)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃; for 1.75h;

DOI:10.1016/S0040-4020(98)01206-X

Reference yield:

acetic acid tert-butyl ester (540-88-5) → {(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 (220567-91-9)

Guidance literature:

Multi-step reaction with 2 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

With diisobutylaluminium hydride; lithium diisopropyl amide; In diethyl ether; hexane;

DOI:10.1016/S0040-4020(98)01206-X

Reference yield:

(4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde (99603-55-1) → {(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 (220567-91-9)

Guidance literature:

Multi-step reaction with 5 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

With (+/-)-camphor sulfonic acid; tin(IV) chloride; diisobutylaluminium hydride; pyridine hydrogenfluoride; lithium diisopropyl amide; In pyridine; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4020(98)01206-X

upstream raw materials:

{(2S,3R)-2-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5-oxo-tetrahydro-furan-3-yl}-acetic acid tert-butyl ester

acetic acid tert-butyl ester

O-(4-methoxybenzyl)-trichloroacetimidate

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

Downstream raw materials:

(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

(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

(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