(2S,3R,4R,5S)-3-benzyloxycarbonylamino-5-O-tert-butyldimethylsilyl-2,4,5-trihydroxy-2,4-O-isopropylidenehexanal

Base Information

Chemical Name:(2S,3R,4R,5S)-3-benzyloxycarbonylamino-5-O-tert-butyldimethylsilyl-2,4,5-trihydroxy-2,4-O-isopropylidenehexanal
CAS No.:1392477-07-4
Molecular Formula:C₂₃H₃₇NO₆Si
Molecular Weight:451.635
Hs Code.:

Synonyms:

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Chemical Property of (2S,3R,4R,5S)-3-benzyloxycarbonylamino-5-O-tert-butyldimethylsilyl-2,4,5-trihydroxy-2,4-O-isopropylidenehexanal

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Technology Process of (2S,3R,4R,5S)-3-benzyloxycarbonylamino-5-O-tert-butyldimethylsilyl-2,4,5-trihydroxy-2,4-O-isopropylidenehexanal

There total 8 articles about (2S,3R,4R,5S)-3-benzyloxycarbonylamino-5-O-tert-butyldimethylsilyl-2,4,5-trihydroxy-2,4-O-isopropylidenehexanal 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:

: C₂₃H₃₇NO₆Si

: 1392477-07-4
(2S,3R,4R,5S)-3-benzyloxycarbonylamino-5-O-tert-butyldimethylsilyl-2,4,5-trihydroxy-2,4-O-isopropylidenehexanal

Guidance literature:: With sodium carbonate; In methanol; at 20 ℃; for 36h; Inert atmosphere;
DOI:10.1039/c2ob25793a

Reference yield:

: 1189128-39-9
(2S,4R,5S,6E)-4-bromo-2-(tert-butyldimethylsilyloxy)-5-hydroxy-6-octen-3-one

: 1392477-07-4
(2S,3R,4R,5S)-3-benzyloxycarbonylamino-5-O-tert-butyldimethylsilyl-2,4,5-trihydroxy-2,4-O-isopropylidenehexanal

Guidance literature:: Multi-step reaction with 7 steps

1: sodium azide / dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere

2: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / -35 - -20 °C / Inert atmosphere

3: pyridinium p-toluenesulfonate / dichloromethane / 20 °C / Inert atmosphere

4: water; trimethylphosphane / tetrahydrofuran / 36 h / 20 °C / Inert atmosphere

5: sodium hydrogencarbonate / methanol / 1.58 h / 0 - 20 °C / Inert atmosphere

6: 2,6-dimethylpyridine; sodium periodate; potassium osmate(VI) dihydrate / 1,4-dioxane; water / 2 h / 20 °C

7: sodium carbonate / methanol / 36 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate; sodium azide; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; sodium carbonate; acetic acid; tetramethylammonium triacetoxyborohydride; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 4: Staudinger reaction;
DOI:10.1039/c2ob25793a

Reference yield:

: 1189128-31-1
(S)-1-bromo-3-(tert-butyldimethylsilyloxy)-2-butanone

: 1392477-07-4
(2S,3R,4R,5S)-3-benzyloxycarbonylamino-5-O-tert-butyldimethylsilyl-2,4,5-trihydroxy-2,4-O-isopropylidenehexanal

Guidance literature:: Multi-step reaction with 8 steps

1.1: titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / -78 °C / Inert atmosphere

1.2: 1.75 h / -78 - -20 °C / Inert atmosphere

2.1: sodium azide / dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere

3.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / -35 - -20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / dichloromethane / 20 °C / Inert atmosphere

5.1: water; trimethylphosphane / tetrahydrofuran / 36 h / 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate / methanol / 1.58 h / 0 - 20 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine; sodium periodate; potassium osmate(VI) dihydrate / 1,4-dioxane; water / 2 h / 20 °C

8.1: sodium carbonate / methanol / 36 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium(IV) isopropylate; potassium osmate(VI) dihydrate; sodium periodate; sodium azide; water; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydrogencarbonate; sodium carbonate; acetic acid; tetramethylammonium triacetoxyborohydride; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 5.1: Staudinger reaction;
DOI:10.1039/c2ob25793a