(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

Base Information

Chemical Name:(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
CAS No.:475276-00-7
Molecular Formula:C₂₂H₃₀O₅
Molecular Weight:374.477
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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:

: 24850-33-7
allyltributylstanane

: 475276-04-1
(3aR,4S,6R,7S,7aR)-6-Allyl-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-carbaldehyde

: (R)-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

: 475276-00-7
(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

Guidance literature:: With lithium perchlorate; In diethyl ether; at 23 ℃; for 23h;
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

: 475276-00-7
(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

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; lithium perchlorate; tetra-(n-butyl)ammonium iodide; 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

: 475276-00-7
(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

Guidance literature:: Multi-step reaction with 6 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

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