5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone

Base Information

Chemical Name:5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone
CAS No.:294204-02-7
Molecular Formula:C₂₉H₃₁N₃O₇
Molecular Weight:533.581
Hs Code.:

Synonyms:5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone

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Chemical Property of 5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone

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Technology Process of 5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone

There total 8 articles about 5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone 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:

: Trifluoro-methanesulfonic acid (S)-1-((2R,3S,4R)-3,4-bis-methoxymethoxy-5-oxo-tetrahydro-furan-2-yl)-2-trityloxy-ethyl ester

: 294204-02-7
5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/jo000141j

Reference yield:

: 56710-46-4,67321-94-2,69602-93-3,94697-68-4,100227-29-0,102355-63-5,121357-95-7
5,6-O-isopropylidene-D-galactonic acid γ-lactone

: 294204-02-7
5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone

Guidance literature:: Multi-step reaction with 7 steps

1.1: 68 percent / iPr₂NEt; n-Bu₄NI / dimethylformamide / 50 °C

2.1: 93 percent / aq. AcOH / 20 °C

3.1: (n-Bu)2SnO; MS 4A / benzene / Heating

3.2: 47 percent / iPr₂NEt / dimethylformamide / 3 h / 20 °C

4.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: 34 percent / NaBH₄ / CH₂Cl₂; methanol / 1 h / -50 °C

6.1: pyridine / CH₂Cl₂ / 2 h / -40 °C

7.1: NaN₃ / dimethylformamide / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: stannylation / 3.2: Substitution / 4.1: Oxidation / 5.1: Reduction / 6.1: Substitution / 7.1: Substitution;
DOI:10.1021/jo000141j

Reference yield:

: 76-83-5
trityl chloride

: 294204-02-7
5-azido-5-deoxy-2,3-di-O-methoxymethyl-6-O-triphenylmethyl-D-galactono-γ-lactone

Guidance literature:: Multi-step reaction with 5 steps

1.1: (n-Bu)2SnO; MS 4A / benzene / Heating

1.2: 47 percent / iPr₂NEt / dimethylformamide / 3 h / 20 °C

2.1: 81 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: 34 percent / NaBH₄ / CH₂Cl₂; methanol / 1 h / -50 °C

4.1: pyridine / CH₂Cl₂ / 2 h / -40 °C

5.1: NaN₃ / dimethylformamide / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; di(n-butyl)tin oxide; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: stannylation / 1.2: Substitution / 2.1: Oxidation / 3.1: Reduction / 4.1: Substitution / 5.1: Substitution;
DOI:10.1021/jo000141j