Eribulin intermediate

Base Information

• Chemical Name: Eribulin intermediate
• CAS No.: 157322-47-9
• Molecular Formula: C21H35IO4
• Molecular Weight: 478.411

Synonyms:[2S-[2alpha,5beta(3S*,5S*)]]-2,2-Dimethylpropanoic acid 3-[tetrahydro-5-(3-hydroxy-6-iodo-5-methyl-6-heptenyl)-4-methylene-2-furanyl]propyl ester

Chemical Property of Eribulin intermediate

Chemical Property:

• Boiling Point: 491.8±45.0 °C(Predicted)
• PKA: 14.89±0.20(Predicted)
• PSA: 55.76000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 5.18560

Purity/Quality:

98%+ ^*data from raw suppliers

[2S-[2α,5β(3S*,5S*)]]-2,2-Dimethyl-PropanoicAcid3-[tetrahydro-5-(3-hydroxy-6-iodo-5-methyl-6-heptenyl)-4-methylene-2-furanyl]propylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: [2S-[2α,5β(3S*,5S*)]]-2,2-Dimethyl-Propanoic Acid 3-[tetrahydro-5-(3-hydroxy-6-iodo-5-methyl-6-heptenyl)-4-methylene-2-furanyl]propyl Ester,can be used in the synthesis of norhalichondrin B.

Technology Process of Eribulin intermediate

There total 50 articles about Eribulin intermediate 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: 92.0%

3-((2S,5S)-4-methylene-5-(3-oxopropyl)tetrahydrofuran-2-yl)propyl pivalate (1443455-05-7) + (3R)-2,4-diiodo-3-methylbut-1-ene (481048-22-0) → 3-((2S,5S)-5-((3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-en-1-yl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate (157322-47-9)

Guidance literature:

With chromium chloride; zirconocene dichloride; cobalt(II) phthalocyanine; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; magnesium; lithium chloride; In 1,2-dimethoxyethane; at 20 - 25 ℃; for 31h; Reagent/catalyst; Glovebox;

Reference yield: 83.0%

(3R,5R)-1-((2S,5S)-5-(3-hydroxypropyl)-3-methylenetetrahydrofuran-2-yl)-6-iodo-5-methylhept-6-en-3-ol (1159006-38-8) + pivaloyl chloride (3282-30-2) → 3-((2S,5S)-5-((3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-en-1-yl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate (157322-47-9)

Guidance literature:

(3R,5R)-1-((2S,5S)-5-(3-hydroxypropyl)-3-methylenetetrahydrofuran-2-yl)-6-iodo-5-methylhept-6-en-3-ol; With 2,4,6-trimethyl-pyridine; dmap; at 0 ℃; for 0.5h; Inert atmosphere;

pivaloyl chloride; at 20 ℃; for 0.75h; Inert atmosphere;

Reference yield:

C17H35NO3Si (914922-88-6) → 3-((2S,5S)-5-((3R,5R)-3-hydroxy-6-iodo-5-methylhept-6-en-1-yl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate (157322-47-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 0 °C / Inert atmosphere

2.1: sodium periodate / tetrahydrofuran; water; tert-butyl alcohol / 6 h / 0 - 20 °C

3.1: chromium dichloride; triethylamine; nickel dichloride / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere; Glovebox

4.1: silver trifluoromethanesulfonate; silver(II) oxide

5.1: tetrahydrofuran / 1 h / -20 - 20 °C / Inert atmosphere

6.1: triethylamine; hydrazine hydrate / ethanol / 2.5 h / 60 - 65 °C

7.1: triethylamine; iodine / diethyl ether / 0 - 20 °C

8.1: hydrogenchloride / methanol; isopropyl alcohol / 3 h / 0 - 20 °C / Inert atmosphere

9.1: 2,4,6-trimethyl-pyridine; dmap / 0.5 h / 0 °C / Inert atmosphere

9.2: 0.75 h / 20 °C / Inert atmosphere

With 2,4,6-trimethyl-pyridine; chromium dichloride; hydrogenchloride; dmap; silver(II) oxide; sodium periodate; osmium(VIII) oxide; hydrazine hydrate; iodine; silver trifluoromethanesulfonate; 4-methylmorpholine N-oxide; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; isopropyl alcohol; tert-butyl alcohol;

upstream raw materials:

(3R,5R)-1-((2S,5S)-5-(3-hydroxypropyl)-3-methylenetetrahydrofuran-2-yl)-6-iodo-5-methylhept-6-en-3-ol

pivaloyl chloride

(2R)-2-[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]oxirane

Downstream raw materials:

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-(((S)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propyl pivalate

3-((2S,5S)-5-(2-((2S,4R,6R)-6-(((2S,3S,4R,5R)-5-((S)-2,3-bis((tert-butyldimethylsilyl)oxy)propyl)-4-methoxy-3-((phenylsulfonyl)methyl)tetrahydrofuran-2-yl)methyl)-4-methyl-5-methylenetetrahydro-2H-pyran-2-yl)ethyl)-4-methylenetetrahydrofuran-2-yl)propan-1-ol

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