ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside

Base Information

Chemical Name:ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside
CAS No.:252951-01-2
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside

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Chemical Property of ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside

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Technology Process of ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside

There total 7 articles about ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside 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: 76.0%

: 874-60-2
4-methyl-benzoyl chloride

: 252951-00-1
ethyl-2,3-dideoxy-3-C-methylene-α,β-D-glycero-pentofuranoside

: 252951-01-2
ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside

Guidance literature:: In pyridine; at 0 ℃; for 3h;
DOI:10.1016/S0008-6215(99)00149-4

Reference yield:

: 107-86-8
3,3-dimethyl acrylaldehyde

: 252951-01-2
ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / NaI; Et₃N / acetonitrile; pentane / 4 h / 40 °C

2: 60 percent / ZnCl₂ / ethyl acetate / 1 h / 20 °C

3: 81 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1 h / 0 - 5 °C

4: (-)-DIPT; Ti(Oi-Pr)4; t-BuOOH / CH₂Cl₂ / 8 h / -20 °C

5: 87 percent / Ti(Oi-Pr)4 / benzene / 2 h / 80 °C

6: 84 percent / HCl / ethanol / 0.5 h / 20 °C

7: 76 percent / pyridine / 3 h / 0 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium iodide; zinc(II) chloride; In pyridine; ethanol; dichloromethane; ethyl acetate; toluene; acetonitrile; pentane; benzene; 1: Substitution / 2: Condensation / 3: Reduction / 4: Epoxidation / 5: Rearrangement / 6: Cyclization / 7: Substitution;
DOI:10.1016/S0008-6215(99)00149-4

Reference yield:

: 69053-98-1
5,5-diethoxy-3-methyl-2-pentenal

: 252951-01-2
ethyl-2,3-dideoxy-3-C-methylene-5-O-toluoyl-α,β-D-glycero-pentofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1 h / 0 - 5 °C

2: (-)-DIPT; Ti(Oi-Pr)4; t-BuOOH / CH₂Cl₂ / 8 h / -20 °C

3: 87 percent / Ti(Oi-Pr)4 / benzene / 2 h / 80 °C

4: 84 percent / HCl / ethanol / 0.5 h / 20 °C

5: 76 percent / pyridine / 3 h / 0 °C

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate; sodium bis(2-methoxyethoxy)aluminium dihydride; In pyridine; ethanol; dichloromethane; toluene; benzene; 1: Reduction / 2: Epoxidation / 3: Rearrangement / 4: Cyclization / 5: Substitution;
DOI:10.1016/S0008-6215(99)00149-4