(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Base Information

Chemical Name:(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol
CAS No.:208662-08-2
Molecular Formula:C₄₁H₅₄O₁₀
Molecular Weight:706.874
Hs Code.:

(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Chemical Property of (4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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Technology Process of (4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

There total 9 articles about (4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-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: 57.0%

: 208662-06-0
(4aR,6R,7R,8S,8aS)-7-[(2S,3S,4R,5R,6S)-3,5-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxine

: 208662-08-2
(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 2h; Ambient temperature;
DOI:10.1080/07328309808002905

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 208662-08-2
(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 4 steps

1: H₂SO₄ / tetrahydrofuran / 20 h / Ambient temperature

2: 1.) Bu₂SnO, 2.) tetra n-butyl ammonium iodide / 1) toluene, reflux, 24 h; 2) THF, reflux, 24 h

3: 71 percent / MS-4 Angstroem, N-iodosuccinimide, trifluoromethanesulfonic acid / toluene / 1 h / -20 °C

4: 57 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS-4 Angstroem; sulfuric acid; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; toluene;
DOI:10.1080/07328309808002905

Reference yield:

: 100-39-0
benzyl bromide

: 208662-08-2
(4aR,6R,7R,8S,8aR)-7-((2S,3S,4R,5S,6S)-3,5-Bis-benzyloxy-4-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-phenyl-6-(2-propyl-pentyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH / 1) DMF, 0 deg C, 30 min; 2) DMF, 2 h

2: 71 percent / MS-4 Angstroem, N-iodosuccinimide, trifluoromethanesulfonic acid / toluene / 1 h / -20 °C

3: 57 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With N-iodo-succinimide; trifluorormethanesulfonic acid; MS-4 Angstroem; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; toluene;
DOI:10.1080/07328309808002905