(Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid

Base Information

Chemical Name:(Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid
CAS No.:143661-48-7
Molecular Formula:C₂₈H₄₂O₈
Molecular Weight:506.637
Hs Code.:

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Chemical Property of (Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid

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Technology Process of (Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid

There total 23 articles about (Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid 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: 87.0%

: 143661-41-0,143661-42-1,143661-46-5,143661-47-6
ethyl (4RS^*,5R^*,6S^*,7S^*,2Z)-7,9-isopropylidenedioxy-4-(p-methoxybenzyloxy)-2,6,8-trimethyl-5-(2-tetrahydropyranyloxy)-2-nonenoate

: 143661-48-7,143661-49-8
(Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid

Guidance literature:: With potassium hydroxide; In methanol; for 48h; Ambient temperature;
DOI:10.1246/bcsj.65.1841

Reference yield:

: 143661-36-3
(2R^*,3S^*,4R^*,5R^*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate

: 143661-48-7,143661-49-8
(Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / H₂ / 10percent Pd/C / ethanol / 8 h

2: 1.) Me₂S complex of copper(I) iodide / 1.) ether, -30 deg C, 2.) ether, 5 deg C, 13 h

3: 89 percent / pyridinium p-toluenesulfonate / benzene / 12 h / Ambient temperature

4: 99 percent / 1 M aq. KOH / methanol / 20 h / Ambient temperature

5: 97 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.17 h / -60 °C

6: 1.) BuLi / 1.) THF, hexane, -20 deg C, 20 min, 2.) THF, hexane, a) -20 deg C, 2 h, b) 5 deg C, 40 h

7: 63 percent / NaH / tetrahydrofuran; dimethylformamide / 16 h / Ambient temperature

8: 55 percent / methyl iodide, calcium carbonate / acetonitrile; H₂O / 40 h / Ambient temperature

9: 1.) sodium hydride / 1.) ether, RT, 1 h, 2.) ether, -20 deg C, 12 h

10: 87 percent / 1 M aq. KOH / methanol / 48 h / Ambient temperature

With potassium hydroxide; n-butyllithium; oxalyl dichloride; copper(I) iodide dimethyl sulfide complex; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; calcium carbonate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1246/bcsj.65.1841

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

: 143661-48-7,143661-49-8
(Z)-(5S,6R)-4-(4-Methoxy-benzyloxy)-2-methyl-5-(tetrahydro-pyran-2-yloxy)-6-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-2-enoic acid

Guidance literature:: Multi-step reaction with 13 steps

1: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

2: 85 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / -78 °C

3: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

4: 99 percent / H₂ / 10percent Pd/C / ethanol / 8 h

5: 1.) Me₂S complex of copper(I) iodide / 1.) ether, -30 deg C, 2.) ether, 5 deg C, 13 h

6: 89 percent / pyridinium p-toluenesulfonate / benzene / 12 h / Ambient temperature

7: 99 percent / 1 M aq. KOH / methanol / 20 h / Ambient temperature

8: 97 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.17 h / -60 °C

9: 1.) BuLi / 1.) THF, hexane, -20 deg C, 20 min, 2.) THF, hexane, a) -20 deg C, 2 h, b) 5 deg C, 40 h

10: 63 percent / NaH / tetrahydrofuran; dimethylformamide / 16 h / Ambient temperature

11: 55 percent / methyl iodide, calcium carbonate / acetonitrile; H₂O / 40 h / Ambient temperature

12: 1.) sodium hydride / 1.) ether, RT, 1 h, 2.) ether, -20 deg C, 12 h

13: 87 percent / 1 M aq. KOH / methanol / 48 h / Ambient temperature

With dmap; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; copper(I) iodide dimethyl sulfide complex; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; calcium carbonate; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1246/bcsj.65.1841