(2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol

Base Information

Chemical Name:(2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol
CAS No.:1392477-01-8
Molecular Formula:C₂₅H₄₁NO₅Si
Molecular Weight:463.69
Hs Code.:

Synonyms:

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Chemical Property of (2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol

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Technology Process of (2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol

There total 6 articles about (2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol 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:

: C₁₇H₃₅NO₃Si

: 501-53-1,94274-21-2
benzyl chloroformate

: 1392477-01-8
(2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol

Guidance literature:: With sodium hydrogencarbonate; In methanol; at 0 - 20 ℃; for 1.58333h; 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

: 1392477-01-8
(2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol

Guidance literature:: Multi-step reaction with 5 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

With sodium azide; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; acetic acid; tetramethylammonium triacetoxyborohydride; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 4: Staudinger reaction;
DOI:10.1039/c2ob25793a

Reference yield:

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

: 1392477-01-8
(2S,3R,4S,5S,6E)-4-amino-N-benzyloxycarbonyl-2-O-tert-butyldimethylsilyl-3,5-O-isopropylidene-6-octene-2,3,5-triol

Guidance literature:: Multi-step reaction with 6 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

With titanium(IV) isopropylate; sodium azide; water; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydrogencarbonate; acetic acid; tetramethylammonium triacetoxyborohydride; trimethylphosphane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetonitrile; 5.1: Staudinger reaction;
DOI:10.1039/c2ob25793a