(2RS^*,3R^*,4S^*,5S^*,6S^*)-5,7-isopropylidenedioxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-(2-tetrahydropyranyloxy)heptanal

Base Information

• Chemical Name: (2RS^*,3R^*,4S^*,5S^*,6S^*)-5,7-isopropylidenedioxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-(2-tetrahydropyranyloxy)heptanal
• CAS No.: 121485-10-7
• Molecular Formula: C₂₅H₃₈O₇
• Molecular Weight: 450.573

Synonyms:

Chemical Property of (2RS^*,3R^*,4S^*,5S^*,6S^*)-5,7-isopropylidenedioxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-(2-tetrahydropyranyloxy)heptanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2RS^*,3R^*,4S^*,5S^*,6S^*)-5,7-isopropylidenedioxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-(2-tetrahydropyranyloxy)heptanal

There total 19 articles about (2RS^*,3R^*,4S^*,5S^*,6S^*)-5,7-isopropylidenedioxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-(2-tetrahydropyranyloxy)heptanal 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: 55.0%

(1RS*,2R*,3S*,4S*,5S*)-1-(1,3-dithian-2-yl)-4,6-isopropylidenedioxy-1-(p-methoxybenzyloxy)-3,5-dimethyl-2-(2-tetrahydropyranyloxy)hexane (143661-40-9,143661-51-2) → (2RS*,3R*,4S*,5S*,6S*)-5,7-isopropylidenedioxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-(2-tetrahydropyranyloxy)heptanal (121485-10-7,143661-45-4)

Guidance literature:

With calcium carbonate; methyl iodide; In water; acetonitrile; for 40h; Ambient temperature;

DOI:10.1246/bcsj.65.1841

Reference yield:

isoprpyl (2R*,3S*,4E)-6-benzyloxy-2-hydroxy-3-methyl-4-hexenoate (120506-06-1,120575-89-5,120575-90-8,120575-91-9,120575-92-0,121570-18-1,143729-26-4,143729-27-5,143729-28-6) → (2RS*,3R*,4S*,5S*,6S*)-5,7-isopropylidenedioxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-(2-tetrahydropyranyloxy)heptanal (121485-10-7,143661-45-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) 1 M aq. KOH, 2.) iodine / 1.) methanol, RT, 1 d, 2.) acetonitrile, 0 deg C, 18 h

2: 90 percent / Na₂CO₃ / 48 h / Ambient temperature

3: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 6 h / Ambient temperature

4: 85 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / -78 °C

5: 99 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

6: 99 percent / H₂ / 10percent Pd/C / ethanol / 8 h

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

8: 89 percent / pyridinium p-toluenesulfonate / benzene / 12 h / Ambient temperature

9: 99 percent / 1 M aq. KOH / methanol / 20 h / Ambient temperature

10: 97 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.17 h / -60 °C

11: 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

12: 63 percent / NaH / tetrahydrofuran; dimethylformamide / 16 h / Ambient temperature

13: 55 percent / methyl iodide, calcium carbonate / acetonitrile; H₂O / 40 h / Ambient temperature

With dmap; potassium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; copper(I) iodide dimethyl sulfide complex; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; sodium carbonate; 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:

(2R*,3S*,4R*,5R*)-6-benzyloxy-4,5-epoxy-3-methyl-2-(2-tetrahydropyranyloxy)hexyl pivalate (143661-36-3) → (2RS*,3R*,4S*,5S*,6S*)-5,7-isopropylidenedioxy-2-(p-methoxybenzyloxy)-4,6-dimethyl-3-(2-tetrahydropyranyloxy)heptanal (121485-10-7,143661-45-4)

Guidance literature:

Multi-step reaction with 8 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

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

upstream raw materials:

(4R,5R)-4-[(1R,2S)-3-[1,3]Dithian-2-yl-3-(4-methoxy-benzyloxy)-1-methyl-2-(tetrahydro-pyran-2-yloxy)-propyl]-2,2,5-trimethyl-[1,3]dioxane

(2S,3R)-2-(Tetrahydro-pyran-2-yloxy)-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butan-1-ol

(2S,3R)-2-(Tetrahydro-pyran-2-yloxy)-3-((4R,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butyraldehyde

2,2-Dimethyl-propionic acid (2S,3R,4R,5R)-4,6-dihydroxy-3,5-dimethyl-2-(tetrahydro-pyran-2-yloxy)-hexyl ester

Downstream raw materials:

(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 ethyl ester

(E)-(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 ethyl ester

ethyl (4RS^*,5R^*,6S^*,7S^*,2Z)-7,9-isopropylidenedioxy-4-(p-methoxybenzyloxy)-2,6,8-trimethyl-5-(2-tetrahydropyranyloxy)-2-nonenoate

ethyl (4RS^*,5R^*,6S^*,7S^*,2E)-7,9-isopropylidenedioxy-4-(p-methoxybenzyloxy)-2,6,8-trimethyl-5-(2-tetrahydropyranyloxy)-2-nonenoate

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