Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester
CAS No.:363139-17-7
Molecular Formula:C₁₉H₂₃N₃O₁₀S
Molecular Weight:485.472
Hs Code.:

Synonyms:Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 1 articles about Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-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: 90.0%

: 108-24-7
acetic anhydride

: 22169-72-8
3-azido-3-deoxy-6-O-toluene-p-sulphonyl-1,2-O-isopropylidene-α-D-glucofuranose

: 363139-17-7
Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: 3-azido-3-deoxy-6-O-toluene-p-sulphonyl-1,2-O-isopropylidene-α-D-glucofuranose; With sulfuric acid; at 60 ℃;

acetic anhydride; With pyridine;
DOI:10.1016/S0040-4039(01)00934-0

Reference yield:

: 363139-17-7
Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

: 363139-22-4
Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-4-azido-2-((2S,3R,4R,5S,6S)-3-benzyloxy-2-bromo-5-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 73 percent / NaCNBH₃; NaI; HMPT / 70 °C

2.1: H₂NNH₃OAc / dimethylformamide / 20 °C

2.2: 85 percent / K₂CO₃ / CH₂Cl₂ / 20 °C

3.1: 75 percent / TMSOTf / CH₂Cl₂ / -50 °C

4.1: Br₂ / CH₂Cl₂ / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; trimethylsilyl trifluoromethanesulfonate; bromine; hydrazinium monoacetate; sodium cyanoborohydride; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)00934-0

Reference yield:

: 363139-17-7
Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-azido-6-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

: 363139-21-3
Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-4-azido-2-((2S,3R,4R,5S,6S)-3-benzyloxy-5-methoxy-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 73 percent / NaCNBH₃; NaI; HMPT / 70 °C

2.1: H₂NNH₃OAc / dimethylformamide / 20 °C

2.2: 85 percent / K₂CO₃ / CH₂Cl₂ / 20 °C

3.1: 75 percent / TMSOTf / CH₂Cl₂ / -50 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; sodium cyanoborohydride; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)00934-0