Acetic acid, [(2S,3S,6R)-2-(1,1-dimethyl-2-oxoethyl)tetrahydro-2-methoxy-3-[(3-nitro benzoyl)oxy]-6-(2-propenyl)-4H-pyran-4-ylidene]-, methyl ester, (2E)-

Base Information

• Chemical Name: Acetic acid, [(2S,3S,6R)-2-(1,1-dimethyl-2-oxoethyl)tetrahydro-2-methoxy-3-[(3-nitro benzoyl)oxy]-6-(2-propenyl)-4H-pyran-4-ylidene]-, methyl ester, (2E)-
• CAS No.: 849744-81-6
• Molecular Formula: C23H27NO9
• Molecular Weight: 461.469
• Mol file: 849744-81-6.mol

Synonyms:

Chemical Property of Acetic acid, [(2S,3S,6R)-2-(1,1-dimethyl-2-oxoethyl)tetrahydro-2-methoxy-3-[(3-nitro benzoyl)oxy]-6-(2-propenyl)-4H-pyran-4-ylidene]-, methyl ester, (2E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid, [(2S,3S,6R)-2-(1,1-dimethyl-2-oxoethyl)tetrahydro-2-methoxy-3-[(3-nitro benzoyl)oxy]-6-(2-propenyl)-4H-pyran-4-ylidene]-, methyl ester, (2E)-

There total 4 articles about Acetic acid, [(2S,3S,6R)-2-(1,1-dimethyl-2-oxoethyl)tetrahydro-2-methoxy-3-[(3-nitro benzoyl)oxy]-6-(2-propenyl)-4H-pyran-4-ylidene]-, methyl ester, (2E)- 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:

3-Nitro-benzoic acid (2S,3S,6R)-6-allyl-2-(2-hydroxy-1,1-dimethyl-ethyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester → 3-Nitro-benzoic acid (2S,3S,6R)-6-allyl-2-(1,1-dimethyl-2-oxo-ethyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester (849744-81-6)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1021/ol0501931

Reference yield:

3-Nitro-benzoic acid (2S,3S,6R)-6-allyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester (849744-77-0) → 3-Nitro-benzoic acid (2S,3S,6R)-6-allyl-2-(1,1-dimethyl-2-oxo-ethyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester (849744-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 900 mg / 3HF*NEt₃ / tetrahydrofuran / 72 h / 20 °C

2: 759 mg / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

With sodium hydrogencarbonate; Dess-Martin periodane; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0501931

Reference yield:

[(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-3-hydroxy-2-methoxy-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester (588728-65-8) → 3-Nitro-benzoic acid (2S,3S,6R)-6-allyl-2-(1,1-dimethyl-2-oxo-ethyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester (849744-81-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 176 mg / DMAP; DIC / CH₂Cl₂ / 20 °C

2: 900 mg / 3HF*NEt₃ / tetrahydrofuran / 72 h / 20 °C

3: 759 mg / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

With dmap; sodium hydrogencarbonate; Dess-Martin periodane; dacarbazine; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0501931

upstream raw materials:

3-Nitro-benzoic acid (2S,3S,6R)-6-allyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

[(2S,6R)-6-Allyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-2-methoxy-3-oxo-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

[(2S,3S,6R)-6-Allyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-1,1-dimethyl-ethyl]-3-hydroxy-2-methoxy-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester

Downstream raw materials:

3-Nitro-benzoic acid (2S,3S,6S)-6-(2,3-bis-triethylsilanyloxy-propyl)-2-((E)-1,1-dimethyl-4-oxo-but-2-enyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

3-Nitro-benzoic acid (2S,3S,6S)-6-(2,3-bis-triethylsilanyloxy-propyl)-2-(1,1-dimethyl-2-oxo-ethyl)-2-methoxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester

Refernces