α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

Base Information

Chemical Name:α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate
CAS No.:201853-28-3
Molecular Formula:C₂₄H₃₀O₄Si
Molecular Weight:410.585
Hs Code.:

Synonyms:α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

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Chemical Property of α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

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Technology Process of α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

There total 8 articles about α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate 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: 90.0%

: 108-24-7
acetic anhydride

: α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranose

: 201853-28-3
α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

Guidance literature:: With pyridine; In dichloromethane;
DOI:10.1016/S0040-4039(97)10531-7

Reference yield:

: 153861-49-5
(1R,2S,4'S)-1-(2',2'-dimethyl-1',3'-dioxolane-4'-yl)-2-(hydroxymethyl)cyclopropane

: 201853-28-3
α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

Guidance literature:: Multi-step reaction with 4 steps

1: DMSO; oxalic chloride; Et₃N / CH₂Cl₂ / 0.25 h / -78 °C

2: 0.1 N HCl / dioxane / 4 h / 20 °C

3: pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 87 percent / pyridine / 0.5 h

With pyridine; hydrogenchloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In 1,4-dioxane; pyridine; dichloromethane; 1: Oxidation / 2: Cyclization / 3: silylation / 4: Acetylation;
DOI:10.1021/jo991212l

Reference yield:

: 201853-25-0
(1S,2R)-2-((S)-2,2-dimethyl[1,3]dioxolan-4-yl)cyclopropane-1-carbaldehyde

: 201853-28-3
α/β-5-O-tert-butyldiphenylsilyl-D-2,3-dideoxy-2,3-endo-methylenepentofuranosyl acetate

Guidance literature:: Multi-step reaction with 3 steps

1: 0.1 N HCl / dioxane / 4 h / 20 °C

2: pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

3: 87 percent / pyridine / 0.5 h

With pyridine; hydrogenchloride; In 1,4-dioxane; pyridine; dichloromethane; 1: Cyclization / 2: silylation / 3: Acetylation;
DOI:10.1021/jo991212l