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

Base Information

Chemical Name:(2E,2'R,3'S,4'Z,6'R,7'S)-3-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenal
CAS No.:863222-63-3
Molecular Formula:C₃₄H₄₆O₆Si
Molecular Weight:578.821
Hs Code.:

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

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

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

There total 6 articles about (2E,2'R,3'S,4'Z,6'R,7'S)-3-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenal 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: 84.0%

: 863222-62-2
(2E,2'R,3'S,4'Z,6'R,7'S)-3-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenol

: 863222-63-3
(2E,2'R,3'S,4'Z,6'R,7'S)-3-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenal

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dimethyl sulfoxide; at 23 ℃; for 1.5h;
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

: 863222-63-3
(2E,2'R,3'S,4'Z,6'R,7'S)-3-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenal

Guidance literature:: Multi-step reaction with 3 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

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; diisobutylaluminium hydride; trimethylphosphane; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 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

: 863222-63-3
(2E,2'R,3'S,4'Z,6'R,7'S)-3-{(2'-allyl-6'-benzyloxy-7'-benzyloxymethyl-2',3',6',7'-tetrahydrooxepin-3'-yl)oxy}-4-(tert-butyldimethylsilyloxy)-2-butenal

Guidance literature:: Multi-step reaction with 5 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

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