Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-tetrahydro-pyran-3-yl ester
CAS No.:289505-47-1
Molecular Formula:C₁₇H₂₁N₃O₆
Molecular Weight:363.37
Hs Code.:

Synonyms:Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-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: 78.0%

: 289505-46-0
Acetic acid (2R,3S,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-4-azido-3-benzyloxy-tetrahydro-pyran-2-yl ester

: 289505-47-1
Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With triethylsilane; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at 20 ℃;
DOI:10.1016/S0040-4039(00)00518-9

Reference yield:

: 100-39-0
benzyl bromide

: 289505-47-1
Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / NaH / dimethylformamide / 0 - 20 °C

2: NaN₃; NH₄Cl / H₂O; 2-methoxy-ethanol / Heating

3: BF₃*Et₂O / 20 °C

4: 78 percent / Et₃SiH; TMSOTF; BF₃*OEt₂ / CH₂Cl₂; acetonitrile / 20 °C

With triethylsilane; sodium azide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium hydride; ammonium chloride; In dichloromethane; 2-methoxy-ethanol; water; N,N-dimethyl-formamide; acetonitrile; 1: Etherification / 2: Ring cleavage / 3: Acetylation / 4: Reduction;
DOI:10.1016/S0040-4039(00)00518-9

Reference yield:

: 213594-43-5
1,6:3,4-dianhydro-2-O-benzyl-β-D-altropyranose

: 289505-47-1
Acetic acid (2R,3S,4R,5S)-2-acetoxymethyl-4-azido-5-benzyloxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: NaN₃; NH₄Cl / H₂O; 2-methoxy-ethanol / Heating

2: BF₃*Et₂O / 20 °C

3: 78 percent / Et₃SiH; TMSOTF; BF₃*OEt₂ / CH₂Cl₂; acetonitrile / 20 °C

With triethylsilane; sodium azide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; ammonium chloride; In dichloromethane; 2-methoxy-ethanol; water; acetonitrile; 1: Ring cleavage / 2: Acetylation / 3: Reduction;
DOI:10.1016/S0040-4039(00)00518-9