(2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

Base Information

Chemical Name:(2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate
CAS No.:1449498-83-2
Molecular Formula:C₂₇H₄₈N₂O₉SSi₂
Molecular Weight:632.923
Hs Code.:

Synonyms:(2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

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Chemical Property of (2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

Chemical Property:

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Technology Process of (2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

There total 7 articles about (2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate 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: 91.0%

: 1449498-82-1
(2Z,5R,6S)-6-amino-5,7-bis{(tert-butyldimethylsilyl)oxy}hept-2-en-1-yl methyl carbonate

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: 1449498-83-2
(2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1039/c3ob42229a

Reference yield:

: (5R,6S)-6-amino-5,7-bis{(tert-butyldimethylsilyl)oxy}hept-2-en-1-yl methyl carbonate

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: 1449498-64-9
(2E,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

: 1449498-83-2
(2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; Overall yield = 84 %; Overall yield = 5.2 g;
DOI:10.3987/COM-12-S(N)99

Reference yield:

: 1301261-30-2
C₂₀H₃₉NO₄Si

: 1449498-83-2
(2Z,5R,6S)-5,7-bis{(tert-butyldimethylsilyl)oxy}-6-(2-nitrophenylsulfonamido)hept-2-en-1-yl methyl carbonate

Guidance literature:: Multi-step reaction with 6 steps

1.1: ozone / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 18 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

2.3: 1 h / -78 °C / Inert atmosphere

3.1: dmap; pyridine / dichloromethane / 13 h / 20 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

6.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; sodium hydride; ozone; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; mineral oil; 2.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1039/c3ob42229a