Eribulin mesylate intermediate

Base Information

• Chemical Name: Eribulin mesylate intermediate
• CAS No.: 157322-83-3
• Molecular Formula: C32H63IO7Si3
• Molecular Weight: 771
• UNII: 5VFM3KRT6E
• Nikkaji Number: J789.302G

Synonyms:157322-83-3;Eribulin mesylate intermediate;Methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate;Methyl 2-[(2S,3R,4S,4aS,6R,8aS)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[(E,1S)-1-[tert-butyl(dimethyl)silyl]oxy-3-iodoprop-2-enyl]-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-6-yl]acetate;5VFM3KRT6E;AMY12387;AC-30649;ER803895;ER-803895;L-ARABINO-D-ALLO-TRIDEC-12-ENONIC ACID, 3,7:6,10-DIANHYDRO-2,4,5,12,13-PENTADEOXY-8,9,11-TRIS-O-((1,1-DIMETHYLETHYL)DIMETHYLSILYL)-13-IODO-, METHYL ESTER, (12E)-;methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis(tert-butyldimethylsilyloxy)-6-((S,E)-1-(tert-butyldimethylsilyloxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate;Methyl2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate

Chemical Property of Eribulin mesylate intermediate

Chemical Property:

• Boiling Point: 608.3±55.0 °C(Predicted)
• PSA: 72.45000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 8.98440
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 14
• Exact Mass: 770.29263
• Heavy Atom Count: 43
• Complexity: 966

Purity/Quality:

99% ^*data from raw suppliers

Methyl2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1C2C(CCC(O2)CC(=O)OC)OC(C1O[Si](C)(C)C(C)(C)C)C(C=CI)O[Si](C)(C)C(C)(C)C
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1[C@@H]2[C@H](CC[C@@H](O2)CC(=O)OC)O[C@H]([C@H]1O[Si](C)(C)C(C)(C)C)[C@H](/C=C/I)O[Si](C)(C)C(C)(C)C
• Uses: Methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate, is an intermediate in the synthesis of Eribulin mesylate (E615203), a synthetic analog of the marine natural product halichondrin B.

Technology Process of Eribulin mesylate intermediate

There total 14 articles about Eribulin mesylate 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: 89.5%

{(2R,4aS,6S,7R,8S,8aS)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[(E)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-allyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-acetic acid methyl ester (185411-11-4) → methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate (157322-83-3)

Guidance literature:

With N-iodo-succinimide; tert-butyldimethylsilyl chloride; In toluene; acetonitrile; at 30 ℃; for 22h;

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-hydroxy-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate → methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate (157322-83-3)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -5 - 0 ℃; for 3h;

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → methyl 2-((2R,4aS,6S,7R,8S,8aS)-7,8-bis((tert-butyldimethylsilyl)oxy)-6-((S,E)-1-((tert-butyldimethylsilyl)oxy)-3-iodoallyl)octahydropyrano[3,2-b]pyran-2-yl)acetate (157322-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 - 25 °C

2: 80 percent / N-iodosuccinimide / acetonitrile; various solvent(s) / Ambient temperature

With 2,6-dimethylpyridine; N-iodo-succinimide; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(96)01999-5

upstream raw materials:

{(2R,4aS,6S,7R,8S,8aS)-7,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[(E)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-trimethylsilanyl-allyl]-octahydro-pyrano[3,2-b]pyran-2-yl}-acetic acid methyl ester

t-butyldimethylsiyl triflate

[(2R,4aS,6S,7S,8R,8aR)-7,8-Dihydroxy-6-((E)-(S)-1-hydroxy-3-trimethylsilanyl-allyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester

C₁₈H₂₆O₇

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