(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester

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Chemical Name:(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester
CAS No.:850835-77-7
Molecular Formula:C₅₃H₅₂O₁₁
Molecular Weight:864.989
Hs Code.:

(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester

Synonyms:(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of (E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of (E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester

There total 10 articles about (E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester 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: 74.0%

: 850835-70-0
iridolactone

: 1-O-(trimethylsilyl)-2-O-benzylcoumaroyl-3,4,6-tris-O-benzyloxy-β-D-glucopyranose

: 850835-77-7
(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -30 ℃; for 120h;
DOI:10.1021/ja050064f

Reference yield:

: (1S,4aS,5S,7S,7aR)-1-Acetoxy-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid

: 850835-77-7
(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 95 mg / 1,3-dicyclohexyl carbodiimide / CH₂Cl₂ / 0.25 h

2: 74 percent / TMSOTf / acetonitrile / 120 h / -30 °C

With trimethylsilyl trifluoromethanesulfonate; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile;
DOI:10.1021/ja050064f

Reference yield:

: (E)-(4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-methyl-oct-2-enedial

: 850835-77-7
(E)-3-(4-Benzyloxy-phenyl)-acrylic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2aS,4S,4aR,5S,7bS)-4-methyl-1-oxo-2a,3,4,4a,5,7b-hexahydro-1H-2,6-dioxa-cyclopenta[cd]inden-5-yloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: L-proline / dimethylsulfoxide / 5 h / 40 °C

1.2: 910 mg / pyridine; DMAP / dimethylsulfoxide / 0.25 h / 0 °C

2.1: POCl₃ / -20 - 20 °C

2.2: 73 percent / 60 h / 40 °C

3.1: 93 percent / NaClO₂; aq. NaH₂PO₄; 2-methylbut-2-ene / 2-methyl-propan-2-ol / 48 h

4.1: HF*pyridine / tetrahydrofuran / 10 h

5.1: 95 mg / 1,3-dicyclohexyl carbodiimide / CH₂Cl₂ / 0.25 h

6.1: 74 percent / TMSOTf / acetonitrile / 120 h / -30 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; L-proline; trichlorophosphate; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol; 1.1: intramolecular Michael addition;
DOI:10.1021/ja050064f