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

Base Information

Chemical Name:(2R,3R,4S,6S)-3-acetoxy-4-(tert-butoxycarbonylamino)-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran
CAS No.:863976-75-4
Molecular Formula:C₃₀H₄₃NO₇Si
Molecular Weight:557.759
Hs Code.:

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

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

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

There total 8 articles about (2R,3R,4S,6S)-3-acetoxy-4-(tert-butoxycarbonylamino)-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: 83.0%

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

: 24424-99-5
di-tert-butyl dicarbonate

: 863976-75-4
(2R,3R,4S,6S)-3-acetoxy-4-(tert-butoxycarbonylamino)-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

Guidance literature:: With hydrogen; triethylamine; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 3h;
DOI:10.1021/jo051086n

Reference yield:

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

: 863976-75-4
(2R,3R,4S,6S)-3-acetoxy-4-(tert-butoxycarbonylamino)-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 7 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

7: 83 percent / hydrogen; triethylamine / Pd/C / ethyl acetate / 3 h / 20 °C

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

Reference yield:

: 863976-78-7
tert-butyl[{(3aR,4R,6S,7aR)-4-methoxy-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl}methoxy]diphenylsilane

: 863976-75-4
(2R,3R,4S,6S)-3-acetoxy-4-(tert-butoxycarbonylamino)-6-[(tert-butyldiphenylsilyloxy)methyl]-2-methoxytetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / acetic acid / H₂O / 17 h / 20 °C

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

3: 80 percent / diisopropyl diazodicarboxylate; triphenylphosphine; diphenylphosphoryl azide / tetrahydrofuran / 50 °C

4: 83 percent / hydrogen; triethylamine / Pd/C / ethyl acetate / 3 h / 20 °C

With pyridine; dmap; di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; hydrogen; acetic acid; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo051086n