2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester

Base Information

Chemical Name:2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester
CAS No.:501432-19-5
Molecular Formula:C₁₄H₁₇N₃O₆S
Molecular Weight:355.371
Hs Code.:

Synonyms:2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester

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Chemical Property of 2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester

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Technology Process of 2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester

There total 7 articles about 2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester 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: 73.0%

: 501432-18-4
2-Azidomethyl-benzoic acid (3aR,5S,6R,6aR)-5-((R)-2-acetoxy-1-acetylsulfanyl-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

: 501432-19-5
2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester

Guidance literature:: With trifluoroacetic acid; In water; at 20 ℃; for 48h;
DOI:10.1081/SCC-120014042

Reference yield:

: 87-41-2
2-benzofuran-1(3H)-one

: 501432-19-5
2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: Ph₃PCl₂ / 2 h / 180 °C

1.2: pyridine / 1 h

2.1: NaN₃ / ethanol; H₂O / 2 h / 60 °C

3.1: NaOH / methanol; H₂O / 3 h

4.1: SOCl₂; N,N-dimethylfomamide / 2 h / 60 °C

5.1: 215 mg / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

6.1: 86 percent / KOAc / 14 h / 140 °C

7.1: 73 percent / trifluoroacetic acid / H₂O / 48 h / 20 °C

With dmap; sodium hydroxide; thionyl chloride; sodium azide; potassium acetate; dichlorotriphenyl-λ⁴-phosphane; N,N-dimethyl-formamide; trifluoroacetic acid; In methanol; ethanol; dichloromethane; water;
DOI:10.1081/SCC-120014042

Reference yield:

: 34040-62-5
o-(chloromethyl)benzoic acid methyl ester

: 501432-19-5
2-Azidomethyl-benzoic acid (2S,3R,4S,5S,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-thiopyran-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NaN₃ / ethanol; H₂O / 2 h / 60 °C

2: NaOH / methanol; H₂O / 3 h

3: SOCl₂; N,N-dimethylfomamide / 2 h / 60 °C

4: 215 mg / 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

5: 86 percent / KOAc / 14 h / 140 °C

6: 73 percent / trifluoroacetic acid / H₂O / 48 h / 20 °C

With dmap; sodium hydroxide; thionyl chloride; sodium azide; potassium acetate; N,N-dimethyl-formamide; trifluoroacetic acid; In methanol; ethanol; dichloromethane; water;
DOI:10.1081/SCC-120014042