(3aS,4S,6R,6aS)-4-Benzyloxy-6-[(E)-3-(2-methoxy-ethoxymethoxy)-propenyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

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Chemical Name:(3aS,4S,6R,6aS)-4-Benzyloxy-6-[(E)-3-(2-methoxy-ethoxymethoxy)-propenyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole
CAS No.:848360-44-1
Molecular Formula:C₂₁H₃₀O₇
Molecular Weight:394.465
Hs Code.:

Synonyms:

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Chemical Property of (3aS,4S,6R,6aS)-4-Benzyloxy-6-[(E)-3-(2-methoxy-ethoxymethoxy)-propenyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

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Technology Process of (3aS,4S,6R,6aS)-4-Benzyloxy-6-[(E)-3-(2-methoxy-ethoxymethoxy)-propenyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

There total 1 articles about (3aS,4S,6R,6aS)-4-Benzyloxy-6-[(E)-3-(2-methoxy-ethoxymethoxy)-propenyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 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:

: 3970-21-6
2-Methoxyethoxymethyl chloride

: 105592-36-7
benzyl (E)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside

: 848360-44-1
(3aS,4S,6R,6aS)-4-Benzyloxy-6-[(E)-3-(2-methoxy-ethoxymethoxy)-propenyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 10h;
DOI:10.1016/S0040-4039(03)00441-6

Reference yield:

: 848360-44-1
(3aS,4S,6R,6aS)-4-Benzyloxy-6-[(E)-3-(2-methoxy-ethoxymethoxy)-propenyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

: 553665-17-1
(E)-(5R,6R,10S)-5,6-Bis-benzyloxy-10-[(S)-1-(2-methoxy-ethoxymethoxy)-heptyl]-3,4,5,6,9,10-hexahydro-oxecin-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: H₂ / Pd-C / methanol / 4 h / 60 °C / 4500.36 Torr

1.2: LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

2.1: 91 percent / pyridine / 0 - 20 °C

3.1: 90 percent / DMF; imidazole / 4 h / 20 °C

4.1: 89 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

5.1: 86 percent / I₂; PPh₃; imidazole / diethyl ether; benzene / 1.5 h / 20 °C

6.1: 96 percent / Zn / ethanol / 1.5 h / Heating

7.1: 85 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

8.1: 88 percent / NaH / CH₂Cl₂ / 0 - 20 °C

9.1: 85 percent / PPTS; t-BuOH / 1.5 h / 80 °C

10.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

11.1: NaClO₂; NaH₂PO₄ / dimethylsulfoxide / 1.5 h / 20 °C

12.1: 76 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

13.1: 67 percent / (PCy₃)2Ru(Cl)2=CH-Ph / CH₂Cl₂ / 28 h / Heating

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; triphenylphosphine; zinc; tert-butyl alcohol; palladium on activated charcoal; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; benzene; 10.1: Swern oxidation;
DOI:10.1016/S0040-4039(03)00441-6

Reference yield:

: 848360-44-1
(3aS,4S,6R,6aS)-4-Benzyloxy-6-[(E)-3-(2-methoxy-ethoxymethoxy)-propenyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

: 553665-15-9
(4R,5R)-4,5-Bis-benzyloxy-hept-6-enoic acid (1S,2S)-1-allyl-2-(2-methoxy-ethoxymethoxy)-octyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: H₂ / Pd-C / methanol / 4 h / 60 °C / 4500.36 Torr

1.2: LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

2.1: 91 percent / pyridine / 0 - 20 °C

3.1: 90 percent / DMF; imidazole / 4 h / 20 °C

4.1: 89 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

5.1: 86 percent / I₂; PPh₃; imidazole / diethyl ether; benzene / 1.5 h / 20 °C

6.1: 96 percent / Zn / ethanol / 1.5 h / Heating

7.1: 85 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

8.1: 88 percent / NaH / CH₂Cl₂ / 0 - 20 °C

9.1: 85 percent / PPTS; t-BuOH / 1.5 h / 80 °C

10.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

11.1: NaClO₂; NaH₂PO₄ / dimethylsulfoxide / 1.5 h / 20 °C

12.1: 76 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; dicyclohexyl-carbodiimide; triphenylphosphine; zinc; tert-butyl alcohol; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; benzene; 10.1: Swern oxidation;
DOI:10.1016/S0040-4039(03)00441-6