2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-yl ester
CAS No.:165805-40-3
Molecular Formula:C₂₃H₂₈N₄O₈S
Molecular Weight:520.563
Hs Code.:

Synonyms:2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-yl ester

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Chemical Property of 2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-yl ester

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Technology Process of 2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-yl ester

There total 5 articles about 2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-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: 89.0%

: 165805-38-9
2-Azidomethyl-benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-6-allyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yl ester

: 507-09-5
tiolacetic acid

: 165805-40-3
2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 25 ℃; for 3h;
DOI:10.1021/ja00106a021

Reference yield:

: 54400-75-8
allyl 2-acetamido-2-deoxy-α-D-glucopyranoside

: 165805-40-3
2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / PPTs / acetonitrile / 1 h / 50 - 55 °C

2: 95 percent / Et₃N, (dimethylamino)pyridine / 12 h / 0 - 25 °C

3: 1.) Me₂BBr, 2.) tetramethylguanidinium azide / 1.) CH₂Cl₂, 25 deg C, 1 h, 2.) acetonitrile, from 0 deg C to 10 deg C, 1 h

4: 89 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 25 °C

With dmap; dimethylboron bromide; di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; triethylamine; triphenylphosphine; tetramethylguanidinum azide; In tetrahydrofuran; acetonitrile;
DOI:10.1021/ja00106a021

Reference yield:

: 70103-17-2
1,1-diethoxy-phthalan

: 165805-40-3
2-Azidomethyl-benzoic acid (2S,3S,4R,5R,6S)-4-acetoxy-5-acetylamino-2-acetylsulfanylmethyl-6-allyloxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / PPTs / acetonitrile / 1 h / 50 - 55 °C

2: 95 percent / Et₃N, (dimethylamino)pyridine / 12 h / 0 - 25 °C

3: 1.) Me₂BBr, 2.) tetramethylguanidinium azide / 1.) CH₂Cl₂, 25 deg C, 1 h, 2.) acetonitrile, from 0 deg C to 10 deg C, 1 h

4: 89 percent / Ph₃P, diisopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 - 25 °C

With dmap; dimethylboron bromide; di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; triethylamine; triphenylphosphine; tetramethylguanidinum azide; In tetrahydrofuran; acetonitrile;
DOI:10.1021/ja00106a021