Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl ester

Base Information

Chemical Name:Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl ester
CAS No.:912352-12-6
Molecular Formula:C₂₈H₃₄O₇
Molecular Weight:482.574
Hs Code.:

Synonyms:Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl ester

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Chemical Property of Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl ester

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Technology Process of Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl ester

There total 15 articles about Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl 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: 88.0%

: 912352-11-5
Benzoic acid (1S,7R,8S)-8-benzyloxy-7-formyloxy-1-methyl-9-oxo-nonyl ester

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 912352-12-6
Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl ester

Guidance literature:: In toluene; for 2h; Heating;
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

: 912352-12-6
Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl ester

Guidance literature:: Multi-step reaction with 8 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

7: 87 percent / H₅IO₆ / ethyl acetate; H₂O / 1 h / 0 °C

8: 88 percent / toluene / 2 h / Heating

With dmap; lithium aluminium tetrahydride; potassium tert-butylate; acetic acid; periodic acid; triethylamine; (S,S)-(salen)manganese; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; 8: Wittig olefination;
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

: 912352-12-6
Benzoic acid (E)-(1S,7R,8R)-8-benzyloxy-7-formyloxy-10-methoxycarbonyl-1-methyl-dec-9-enyl ester

Guidance literature:: Multi-step reaction with 7 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

6: 87 percent / H₅IO₆ / ethyl acetate; H₂O / 1 h / 0 °C

7: 88 percent / toluene / 2 h / Heating

With dmap; lithium aluminium tetrahydride; acetic acid; periodic acid; triethylamine; (S,S)-(salen)manganese; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; 7: Wittig olefination;
DOI:10.1016/j.tetlet.2006.07.043