(2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene

Base Information

Chemical Name:(2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene
CAS No.:1609460-88-9
Molecular Formula:C₆₉H₉₃NO₁₁
Molecular Weight:1112.5
Hs Code.:

Synonyms:(2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene

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Chemical Property of (2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene

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Technology Process of (2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene

There total 9 articles about (2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene 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:

: 1609460-81-2
dimethyl [(3,4,5,7-tetra-O-benzyl-6-O-p-methoxybenzyloxy-D-galacto)-1-oxomethyl]phosphonate

: 799268-00-1
2-[N-(tert-butoxycarbonyl)amino]-3,4-O-isopropylideneoctadecan-1-al

: 1609460-88-9
(2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene

Guidance literature:: With potassium carbonate; In ethanol; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo500769f

Reference yield:

: 799267-98-4
1-N-tert-butyloxycarbonyl-3,4-O-isopropylidene-phytosphingosine

: 1609460-88-9
(2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere

2: potassium carbonate / ethanol / 1 h / 20 °C / Inert atmosphere

With sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; In ethanol; dichloromethane; 2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/jo500769f

Reference yield:

: 3,4,5,7-tetra-O-benzyl-6-O-p-methoxybenzyloxy-D-galactohept-1-ene

: 1609460-88-9
(2E,3S,4S,5R)-3-[N-(tert-butoxycarbonyl)amino]-4,5-O-isopropylidene-1-anhydro(2,3,4,6-tetra-O-benzyl-5-O-p-methoxybenzyloxy-D-galacto)-2-nonadecene

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium periodate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.1: potassium carbonate / ethanol / 1 h / 20 °C / Inert atmosphere

With sodium periodate; n-butyllithium; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; ethanol; dichloromethane; 4.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/jo500769f