Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 220608-71-9
• Molecular Formula: C₂₅H₂₈O₇
• Molecular Weight: 440.493

Synonyms:Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property of Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

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Technology Process of Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 8 articles about Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 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: 94.0%

benzaldehyde dimethyl acetal (1125-88-8) + Benzoic acid (2R,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester (220608-66-2) → Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (220608-71-9)

Guidance literature:

With camphor-10-sulfonic acid;

DOI:10.1021/ja9832358

Reference yield:

bromide 2,3,4,6-tetra-O-Bz-α-D-galactopyranosyl bromide (188435-38-3) → Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (220608-71-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / silver triflate, molecular sieves (4 Angstroem) / CH₂Cl₂ / 0.5 h / -20 °C

2: 96 percent / MeOH / NaOMe

3: 44 percent / HCOOH / 2 h / Ambient temperature

4: n-Bu₄NHSO₄, 40percent aq. NaOH / 0.17 h / 0 °C

With methanol; sodium hydroxide; formic acid; 4 A molecular sieve; silver trifluoromethanesulfonate; tetra(n-butyl)ammonium hydrogensulfate; sodium methylate; In dichloromethane;

DOI:10.1016/S0040-4020(01)81568-4

Reference yield:

Benzoic acid (4aR,6R,7R,8R,8aS)-7-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester → Benzoic acid (2S,4aR,6R,7R,8S,8aR)-8-hydroxy-6-pent-4-enyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (220608-71-9)

Guidance literature:

With sodium hydroxide; In acetone; at 0 ℃; for 0.166667h; Yield given;

DOI:10.1016/S0040-4020(01)81568-4

upstream raw materials:

benzaldehyde dimethyl acetal

Benzoic acid (2R,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester

n-Pent-4-enyl alcohol

2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide

Downstream raw materials:

pent-4-enyl 2-O-benzoyl-4,6-O-benzylidene-3-O-chloroacetyl-β-D-galactopyranoside

C₄₆H₄₅Br₂ClO₁₄

C₄₄H₄₄Br₂O₁₃

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