(S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one

Base Information

• Chemical Name: (S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one
• CAS No.: 220567-79-3
• Molecular Formula: C₁₄H₂₄O₅Si
• Molecular Weight: 300.427
• Mol file: 220567-79-3.mol

Synonyms:(S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one

Chemical Property of (S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one

There total 1 articles about (S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one 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: 71.0%

(furan-2-yloxy)-trimethylsilane (61550-02-5) + (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-carbaldehyde (99603-55-1) → (S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one (220567-79-3)

Guidance literature:

With tin(IV) chloride; In dichloromethane; at -78 ℃; for 15h;

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

Reference yield:

(S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one (220567-79-3) → {(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)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / HF*pyridine / pyridine / 0.17 h / 0 °C

2: 75 percent / (+/-)-camphor sulfonic acid / CH₂Cl₂ / 69 h / Ambient temperature

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

With (+/-)-camphor sulfonic acid; pyridine hydrogenfluoride; lithium diisopropyl amide; In pyridine; dichloromethane;

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

Reference yield:

(S)-5-[(R)-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxolan-4-yl)-trimethylsilanyloxy-methyl]-5H-furan-2-one (220567-79-3) → {(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 4 steps

1: 80 percent / HF*pyridine / pyridine / 0.17 h / 0 °C

2: 75 percent / (+/-)-camphor sulfonic acid / CH₂Cl₂ / 69 h / Ambient temperature

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

4: 50 percent / DIBAL / diethyl ether; hexane / 1.75 h / -78 °C

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

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

upstream raw materials:

(furan-2-yloxy)-trimethylsilane

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

Downstream raw materials:

(S)-5-[(R)-(4-Methoxy-benzyloxy)-((4S,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methyl]-5H-furan-2-one

{(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

{(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

(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