(2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile

Base Information

Chemical Name:(2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile
CAS No.:863222-47-3
Molecular Formula:C₃₅H₄₇NO₅Si
Molecular Weight:589.847
Hs Code.:

Synonyms:(2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile

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Chemical Property of (2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile

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Technology Process of (2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile

There total 8 articles about (2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile 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: 63.0%

: 863222-48-4
(3E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)-2-(trimethylsilyloxy)pent-3-enenitrile

: 863222-47-3
(2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile

Guidance literature:: With boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; In dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 863222-50-8
(2R,3S,4Z,6R,7S)-2-allyl-6-benzyloxy-7-benzyloxymethyl-2,3,6,7-tetrahydrooxepin-3-ol

: 863222-47-3
(2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / PMe₃ / tetrahydrofuran; CH₂Cl₂ / 0.5 h / 24 °C

2: 94 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

3: 84 percent / TPAP; NMO; 4 Angstroem molecular sieves / dimethylsulfoxide / 1.5 h / 23 °C

4: 74 percent / Me₃Al / benzene; hexane / 1 h / 25 °C

5: 63 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; trimethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; benzene; 1: hetero-Michael addition;
DOI:10.1016/j.tet.2005.05.073

Reference yield:

: 863222-60-0
(2R,3S,4Z,6R,7S)-{6-benzyloxy-7-benzyloxymethyl-3-(4-methoxybenzyloxy)-2,3,6,7-tetrahydrooxepin-2-yl}ethanal

: 863222-47-3
(2E,2'R,3'S,4'Z,6'R,7'S)-4-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-5-(tert-butyldimethylsilyloxy)pent-2-enenitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaHMDS / tetrahydrofuran / 1 h / 20 °C

1.2: 100 percent / tetrahydrofuran / -78 - 22 °C

2.1: 92 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 0 °C / pH 7

3.1: 98 percent / PMe₃ / tetrahydrofuran; CH₂Cl₂ / 0.5 h / 24 °C

4.1: 94 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

5.1: 84 percent / TPAP; NMO; 4 Angstroem molecular sieves / dimethylsulfoxide / 1.5 h / 23 °C

6.1: 74 percent / Me₃Al / benzene; hexane / 1 h / 25 °C

7.1: 63 percent / Bu₃SnH; BF₃*Et₂O / CH₂Cl₂ / 0.17 h / 0 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; trimethylaluminum; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; benzene; 1.2: Wittig reaction / 3.1: hetero-Michael addition;
DOI:10.1016/j.tet.2005.05.073