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

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 220608-66-2
• Molecular Formula: C₁₈H₂₄O₇
• Molecular Weight: 352.384

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

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

Chemical Property:

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

There total 3 articles about Benzoic acid (2R,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-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:

(2S,3aR,5R,6R,7S,7aR)-5-Hydroxymethyl-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol → Benzoic acid (2R,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester (220608-66-2)

Guidance literature:

With pentenyl alcohol; triethylsilyl trifluoromethyl sulfonate; for 4h; Yield given; Ambient temperature;

DOI:10.1021/ja9832358

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → Benzoic acid (2R,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester (220608-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₄NI, lutidine, 2.) NaOMe, 3.) TESOTf

2: TESOTf, pentenyl alcohol / 4 h / Ambient temperature

With lutidine; pentenyl alcohol; triethylsilyl trifluoromethyl sulfonate; sodium methylate; tetra-(n-butyl)ammonium iodide;

DOI:10.1021/ja9832358

Reference yield:

2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide (61198-88-7) → Benzoic acid (2R,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester (220608-66-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₄NI, lutidine, 2.) NaOMe, 3.) TESOTf

2: TESOTf, pentenyl alcohol / 4 h / Ambient temperature

With lutidine; pentenyl alcohol; triethylsilyl trifluoromethyl sulfonate; sodium methylate; tetra-(n-butyl)ammonium iodide;

DOI:10.1021/ja9832358

upstream raw materials:

n-Pent-4-enyl alcohol

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

Downstream raw materials:

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

C₄₆H₄₅Br₂ClO₁₄

C₄₄H₄₄Br₂O₁₃

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