methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose
CAS No.:122672-66-6
Molecular Formula:C₁₉H₂₄O₇
Molecular Weight:364.395
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

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Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

There total 1 articles about methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose 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: 78.0%

: 122672-65-5
methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose

: 74-88-4
methyl iodide

: 122672-66-6
methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

Guidance literature:: With potassium hydride; In tetrahydrofuran;
DOI:10.1039/c39900001440

Reference yield:

: 122672-66-6
methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

: 122622-27-9
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(formylmethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 2.) LiAlH₄ / 1.) THF, 15 min, 2.) THF, 0 deg C, 45 min

2: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

3: 69 percent / SOCl₂, pyridine / tetrahydrofuran / 1 h / 0 °C

4: dimethylformamide / 2 h / 100 °C

5: NaOMe / methanol / Ambient temperature

6: PCC, AcONa, Celite / CH₂Cl₂ / 0.33 h / Ambient temperature

7: tetrahydrofuran / 0.17 h

8: Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 0.08 h / Ambient temperature

9: MeLi / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

10: mercuric trifluoroacetate / Ambient temperature

11: xylene / 24 h / Heating

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; thionyl chloride; Celite; methyllithium; sodium methylate; sodium acetate; mercury(II) trifluoroacetate; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; xylene;
DOI:10.1021/jo00283a034

Reference yield:

: 122672-66-6
methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose

: 122592-17-0
methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2-deoxy-2-C-methyl-3-C-vinyl-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 2.) LiAlH₄ / 1.) THF, 15 min, 2.) THF, 0 deg C, 45 min

2: imidazole / tetrahydrofuran / 0.5 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; In tetrahydrofuran;
DOI:10.1021/jo00283a034