(3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Base Information

Chemical Name:(3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
CAS No.:475276-05-2
Molecular Formula:C₂₉H₃₆O₅
Molecular Weight:464.602
Hs Code.:

Synonyms:(3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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Chemical Property of (3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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Technology Process of (3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

There total 9 articles about (3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran 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: 100.0%

: 100-39-0
benzyl bromide

: 475276-00-7
(S)-1-((3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-but-3-en-1-ol

: 475276-05-2
(3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 25 ℃; for 22h;
DOI:10.1055/s-2002-33511

Reference yield:

: 53263-18-6,82659-53-8,98920-46-8,98920-48-0,98920-49-1,103773-87-1,98920-44-6
allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

: 475276-05-2
(3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: Multi-step reaction with 8 steps

1: 89 percent / MeONa / methanol / 48 h / 0 °C

2: imidazole / dimethylformamide / 0.5 h / 24 °C

3: CSA / 1.5 h / 24 °C

4: 99 percent / NaI; Bu₄NI / tetrahydrofuran / 30 h / 24 °C

5: 100 percent / TBAF / tetrahydrofuran / 2 h / 23 °C

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.42 h / -78 - 0 °C

7: LiClO₄ / diethyl ether / 23 h / 23 °C

8: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 22 h / 25 °C

With 1H-imidazole; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; lithium perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 6: Swern oxidation;
DOI:10.1055/s-2002-33511

Reference yield:

: 133697-14-0
2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enitol

: 475276-05-2
(3aS,4R,6R,7S,7aR)-6-Allyl-7-benzyloxy-4-((S)-1-benzyloxy-but-3-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole / dimethylformamide / 0.5 h / 24 °C

2: CSA / 1.5 h / 24 °C

3: 99 percent / NaI; Bu₄NI / tetrahydrofuran / 30 h / 24 °C

4: 100 percent / TBAF / tetrahydrofuran / 2 h / 23 °C

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.42 h / -78 - 0 °C

6: LiClO₄ / diethyl ether / 23 h / 23 °C

7: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 22 h / 25 °C

With 1H-imidazole; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; lithium perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 5: Swern oxidation;
DOI:10.1055/s-2002-33511