(2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

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Chemical Name:(2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran
CAS No.:863976-81-2
Molecular Formula:C₂₅H₃₃N₃O₅Si
Molecular Weight:483.64
Hs Code.:

Synonyms:(2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

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Chemical Property of (2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

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Technology Process of (2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

There total 7 articles about (2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran 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: 80.0%

: 863976-80-1
(2R,3R,4R,6S)-3-acetoxy-6-[(tert-butyldiphenylsilyloxy)methyl]-4-hydroxy-2-methoxytetrahydro-2H-pyran

: 863976-81-2
(2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

Guidance literature:: With di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; triphenylphosphine; In tetrahydrofuran; at 50 ℃;
DOI:10.1021/jo051086n

Reference yield:

: 863976-76-5
(3R,4R,6S)-6-[(tert-butyldiphenylsilyloxy)methyl]-3,4-dihydroxytetrahydropyran-2-one

: 863976-81-2
(2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / Et₂O*BF₃ / acetone / 3 h / 20 °C

2: DIBAL-H / toluene / 1.5 h / -78 °C

3: 1.34 g / Ag₂O / CH₂Cl₂ / 3 h / 20 °C

4: 78 percent / acetic acid / H₂O / 17 h / 20 °C

5: 78 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 2 h / 20 °C

6: 80 percent / diisopropyl diazodicarboxylate; triphenylphosphine; diphenylphosphoryl azide / tetrahydrofuran / 50 °C

With pyridine; dmap; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; diphenylphosphoranyl azide; diisobutylaluminium hydride; acetic acid; triphenylphosphine; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo051086n

Reference yield:

: 863976-79-8
(2R,3R,4R,6S)-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran-3,4-diol

: 863976-81-2
(2R,3R,4S,6S)-3-acetoxy-4-azido-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: 78 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 80 percent / diisopropyl diazodicarboxylate; triphenylphosphine; diphenylphosphoryl azide / tetrahydrofuran / 50 °C

With pyridine; dmap; di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo051086n