(2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone

Base Information

Chemical Name:(2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone
CAS No.:108470-06-0
Molecular Formula:C₁₇H₂₂O₃
Molecular Weight:274.36
Hs Code.:

Synonyms:(2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone

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Chemical Property of (2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone

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Technology Process of (2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone

There total 19 articles about (2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone 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:

: 26291-75-8,81114-49-0,109200-09-1,128461-80-3
(R)-1-((3aR,5S,6R,6aR)-2,2,6-trimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

: 108470-06-0
(2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone

Guidance literature:: Multi-step reaction with 9 steps

1: 1) p-toluenesulfonyl chloride, pyridine; 2) K₂CO₃ / 1) 17 h; 2) MeOH, r.t., 40 min

2: 81 percent / lithium aluminium hydride / diethyl ether / 5 h, 0 deg C, then 1 h r.t.

3: 92 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

4: 100 percent / tetrahydrofuran / 2 h / 18 °C

5: BH₃-THF / tetrahydrofuran / 1 h / 0 - 5 °C

6: 89 percent / NaH / dimethylsulfoxide / 20 h / Ambient temperature

7: 83 percent / aq. HCl / tetrahydrofuran / 10.5 h / 40 °C

8: 94.4 percent / NaIO₄ / methanol; H₂O / 1 h / 0 °C

9: 1) NaH; 2) K₂CO₃ / 1) THF, -80 deg C, then 8 deg C; 2) MeOH, r.t., 1 h

With pyridine; hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; borane-THF; 3 A molecular sieve; sodium hydride; potassium carbonate; p-toluenesulfonyl chloride; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2184

Reference yield:

: 56982-95-7
(3aR,5S,6R,6aR)-2,2,6-trimethyl-5-((R)-oxiran-2-yl)tetrahydrofuro[2,3-d][1,3]dioxole

: 108470-06-0
(2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / lithium aluminium hydride / diethyl ether / 5 h, 0 deg C, then 1 h r.t.

2: 92 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

3: 100 percent / tetrahydrofuran / 2 h / 18 °C

4: BH₃-THF / tetrahydrofuran / 1 h / 0 - 5 °C

5: 89 percent / NaH / dimethylsulfoxide / 20 h / Ambient temperature

6: 83 percent / aq. HCl / tetrahydrofuran / 10.5 h / 40 °C

7: 94.4 percent / NaIO₄ / methanol; H₂O / 1 h / 0 °C

8: 1) NaH; 2) K₂CO₃ / 1) THF, -80 deg C, then 8 deg C; 2) MeOH, r.t., 1 h

With hydrogenchloride; sodium periodate; lithium aluminium tetrahydride; borane-THF; 3 A molecular sieve; sodium hydride; potassium carbonate; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2184

Reference yield:

: 114144-67-1
6-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-allofuranose

: 108470-06-0
(2Z,4S,5S,6S)-7-O-benzyloxy-5-hydroxy-2,4,6-trimethylhept-2-enoic acid δ-lactone

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH₂Cl₂ / 24 h / Ambient temperature

2: 85 percent / tetrahydrofuran / Ambient temperature

3: 1) H₂, 5 percent Rh-Al₂O₃; 2) H₂, 10 percent Pd-C / 1) EtOH, 8-10 deg C; 2) EtOH, r.t., 6 h

4: 89 percent / NaH / dimethylsulfoxide / 20 h / Ambient temperature

5: 83 percent / aq. HCl / tetrahydrofuran / 10.5 h / 40 °C

6: 94.4 percent / NaIO₄ / methanol; H₂O / 1 h / 0 °C

7: 1) NaH; 2) K₂CO₃ / 1) THF, -80 deg C, then 8 deg C; 2) MeOH, r.t., 1 h

With hydrogenchloride; sodium periodate; palladium on activated charcoal; rhodium on alumina; 3 A molecular sieve; hydrogen; sodium hydride; potassium carbonate; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;
DOI:10.1248/cpb.35.2184