5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-lactone

Base Information

Chemical Name:5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-lactone
CAS No.:1395068-35-5
Molecular Formula:C₂₁H₂₃N₃O₇S
Molecular Weight:461.496
Hs Code.:

Synonyms:5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-lactone

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Chemical Property of 5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-lactone

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Technology Process of 5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-lactone

There total 8 articles about 5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-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: 93.0%

: 1395068-33-3
5-azido-3,6-di-O-benzyl-5-deoxy-L-gulono-1,4-lactone

: 124-63-0
methanesulfonyl chloride

: 1395068-35-5
5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-lactone

Guidance literature:: With pyridine; at 0 - 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo301243s

Reference yield:

: 130619-55-5
5-azido-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose

: 1395068-35-5
5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-lactone

Guidance literature:: Multi-step reaction with 6 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 17 h / -10 - 20 °C / Inert atmosphere

2: toluene-4-sulfonic acid / water; 1,4-dioxane / 2.5 h / 80 °C

3: iodine; potassium carbonate / tert-butyl alcohol / 2 h / 100 °C

4: pyridine / dichloromethane / 1 h / -40 °C / Inert atmosphere

5: sodium 2,2,2-trifluoroacetate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

6: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; iodine; sodium 2,2,2-trifluoroacetate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;
DOI:10.1021/jo301243s

Reference yield:

: 115351-15-0
1,2-O-isopropylidene-3,6-di-O-benzyl-5-azido-5-deoxy-β-L-idofuranose

: 1395068-35-5
5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-L-gulono-1,4-lactone

Guidance literature:: Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid / water; 1,4-dioxane / 2.5 h / 80 °C

2: iodine; potassium carbonate / tert-butyl alcohol / 2 h / 100 °C

3: pyridine / dichloromethane / 1 h / -40 °C / Inert atmosphere

4: sodium 2,2,2-trifluoroacetate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

5: pyridine / 2 h / 0 - 20 °C / Inert atmosphere

With pyridine; iodine; sodium 2,2,2-trifluoroacetate; potassium carbonate; toluene-4-sulfonic acid; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo301243s