(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)-2-pentenal

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)-2-pentenal
CAS No.:863222-64-4
Molecular Formula:C₃₅H₄₈O₆Si
Molecular Weight:592.848
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)-2-pentenal

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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)-2-pentenal

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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)-2-pentenal

There total 9 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)-2-pentenal 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: 83.0%

: 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

: 863222-64-4
(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)-2-pentenal

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;
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

: 863222-64-4
(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)-2-pentenal

Guidance literature:: Multi-step reaction with 6 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

6: 83 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °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

: 863222-64-4
(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)-2-pentenal

Guidance literature:: Multi-step reaction with 8 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

8.1: 83 percent / DIBAH / CH₂Cl₂; hexane / 1 h / -78 °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