(4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Base Information

Chemical Name:(4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
CAS No.:753502-54-4
Molecular Formula:C₂₁H₃₀O₆
Molecular Weight:378.466
Hs Code.:

Synonyms:(4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Chemical Property of (4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Technology Process of (4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

There total 4 articles about (4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 86.0%

: 77-76-9
2,2-dimethoxy-propane

: 753502-53-3
(2R,3S,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-isopropoxy-2-vinyl-tetrahydro-pyran-3,5-diol

: 753502-54-4
(4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: With camphor-10-sulfonic acid; In acetone; at 20 ℃;
DOI:10.1016/j.tet.2004.06.009

Reference yield:

: 612841-73-3
1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside

: 753502-54-4
(4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 76 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / -78 - 20 °C

2: sodium; MeOH / 16 h / 20 °C

3: 86 percent / camphorsulfonic acid / acetone / 20 °C

With methanol; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; sodium; In dichloromethane; acetone;
DOI:10.1016/j.tet.2004.06.009

Reference yield:

: 612841-85-7
isopropyl 2,4,6-tri-O-acetyl-3-O-benzyl-5-C-vinyl-β-D-glucopyranoside

: 753502-54-4
(4aR,6R,7R,8R,8aS)-8-Benzyloxy-6-isopropoxy-2,2-dimethyl-4a-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: Multi-step reaction with 2 steps

1: sodium; MeOH / 16 h / 20 °C

2: 86 percent / camphorsulfonic acid / acetone / 20 °C

With methanol; camphor-10-sulfonic acid; sodium; In acetone;
DOI:10.1016/j.tet.2004.06.009