Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

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Chemical Name:Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester
CAS No.:641613-77-6
Molecular Formula:C₂₆H₃₄O₇
Molecular Weight:458.552
Hs Code.:

Synonyms:Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

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Chemical Property of Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

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Technology Process of Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

There total 9 articles about Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl 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: 96.0%

: 641613-72-1
Acetic acid (E)-(4R,5R)-7-(tert-butyl-dimethyl-silanyloxy)-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

: 641613-77-6
Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/j.tetlet.2003.09.141

Reference yield:

: 94844-33-4
ethyl (E)-5-((tert-butyldimethylsilyl)oxy)pent-2-enoate

: 641613-77-6
Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: (dihydroquinidine)2-phthalazine; potassium osmate; aq. potassium ferricyanide / K₂CO₃ / 2-methyl-propan-2-ol / 12 h / 20 °C

2: BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.33 g / LiAlH₄ / diethyl ether / 1 h / 20 °C

4: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 546 mg / CH₂Cl₂ / 4 h / Heating

6: DIBAL / diethyl ether / 12 h / -78 - 20 °C

7: 1.18 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

8: TBAF / tetrahydrofuran / 24 h / 20 °C

With dmap; potassium osmate(VI); lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 4: Swern oxidation / 5: Wittig olefination;
DOI:10.1002/chem.200500892

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 641613-77-6
Acetic acid (E)-(4R,5R)-7-hydroxy-4,5-bis-(4-methoxy-benzyloxy)-2-methyl-hept-2-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.33 g / LiAlH₄ / diethyl ether / 1 h / 20 °C

3: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: 546 mg / CH₂Cl₂ / 4 h / Heating

5: DIBAL / diethyl ether / 12 h / -78 - 20 °C

6: 1.18 g / Et₃N; DMAP / CH₂Cl₂ / 3 h / 20 °C

7: TBAF / tetrahydrofuran / 24 h / 20 °C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3: Swern oxidation / 4: Wittig olefination;
DOI:10.1002/chem.200500892