Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl ester

Base Information

Chemical Name:Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl ester
CAS No.:912352-10-4
Molecular Formula:C₂₅H₃₂O₆
Molecular Weight:428.525
Hs Code.:

Synonyms:Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl ester

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Chemical Property of Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl ester

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Technology Process of Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl ester

There total 13 articles about Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl 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: 82.0%

: 912352-09-1
Benzoic acid (S)-6-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-methyl-hexyl ester

: 912352-10-4
Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl ester

Guidance literature:: With acetic acid; at 70 ℃; for 12h;
DOI:10.1016/j.tetlet.2006.07.043

Reference yield:

: 912351-95-2
6-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-hexanal

: 912352-10-4
Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / t-BuOK / dimethylsulfoxide / 1 h / 0 °C

2: 41 percent / S,S-Jacobsen catalyst / H₂O / 12 h / 20 °C

3: 71 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

4: 75 percent / LAH / tetrahydrofuran / 1 h / 0 °C

5: 78 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

6: 82 percent / aq. AcOH / 12 h / 70 °C

With dmap; lithium aluminium tetrahydride; potassium tert-butylate; acetic acid; triethylamine; (S,S)-(salen)manganese; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2006.07.043

Reference yield:

: 912351-99-6
(3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(5-oxiranyl-pentyl)-tetrahydro-furo[2,3-d][1,3]dioxole

: 912352-10-4
Benzoic acid (S)-6-((2R,3R,4R,5S)-3-benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-methyl-hexyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 41 percent / S,S-Jacobsen catalyst / H₂O / 12 h / 20 °C

2: 71 percent / Et₃N / CH₂Cl₂ / 12 h / 0 °C

3: 75 percent / LAH / tetrahydrofuran / 1 h / 0 °C

4: 78 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 °C

5: 82 percent / aq. AcOH / 12 h / 70 °C

With dmap; lithium aluminium tetrahydride; acetic acid; triethylamine; (S,S)-(salen)manganese; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tetlet.2006.07.043