5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene

Base Information

• Chemical Name: 5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene
• CAS No.: 108470-24-2
• Molecular Formula: C₂₆H₄₂O₆
• Molecular Weight: 450.616

Synonyms:5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene

Chemical Property of 5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene

Chemical Property:

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Technology Process of 5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene

There total 13 articles about 5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene 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: 70.0%

5(R)-<5(R)-(2-hydroxyethyl)-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl>-4(R)-hydroxy-1-hexane (113919-01-0) + 4-chloromethyl-1,2-dimethoxy-benzene (7306-46-9) → 5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene (108470-24-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; for 11h; Ambient temperature;

DOI:10.1248/cpb.35.2219

Reference yield:

3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (58399-55-6) → 5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene (108470-24-2)

Guidance literature:

Multi-step reaction with 12 steps

1: LiAlH₄

2: NaH

3: 92 percent / H₂SO₄ / methanol / Ambient temperature

4: 1) imidazole; 2) DMSO, (COCl)2, Et₃N; 3)

5: 1) BH₃; 2) aq. H₂O₂, NaOH; 3) TsCl, pyridine; 4) LiAlH₄

6: 1) NaH; 2) aq. H₂SO₄; 3) NaIO₄

7: 1) NaH; 2) K₂CO₃; 3) diisobutylaluminium hydride; 4) camphorsulfonic acid

8: 81 percent / H₂ / Raney-Ni / ethanol

9: 1) imidazole; 2) H₂ / 2) Pd-C / 1) CH₂Cl₂

10: 100 percent / DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / -60 °C

11: 78 percent / CrCl₂ / 0 °C

12: 1) n-Bu₄NF; 2) NaH / 1) THF

With pyridine; 1H-imidazole; chromium dichloride; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; borane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; palladium on activated charcoal; nickel; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)84872-8

Reference yield:

1,2;5,6-di-O-isopropylidene-3-(2-hydroxyethyl)-α-D-allofuranoside (18427-19-5) → 5(S)-(5(R)-<2-(3,4-dimethoxybenzyloxy)ethyl>-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl)-4(R)-hydroxy-1-hexene (108470-24-2)

Guidance literature:

Multi-step reaction with 11 steps

1: NaH

2: 92 percent / H₂SO₄ / methanol / Ambient temperature

3: 1) imidazole; 2) DMSO, (COCl)2, Et₃N; 3)

4: 1) BH₃; 2) aq. H₂O₂, NaOH; 3) TsCl, pyridine; 4) LiAlH₄

5: 1) NaH; 2) aq. H₂SO₄; 3) NaIO₄

6: 1) NaH; 2) K₂CO₃; 3) diisobutylaluminium hydride; 4) camphorsulfonic acid

7: 81 percent / H₂ / Raney-Ni / ethanol

8: 1) imidazole; 2) H₂ / 2) Pd-C / 1) CH₂Cl₂

9: 100 percent / DMSO, (COCl)2, NEt₃ / CH₂Cl₂ / -60 °C

10: 78 percent / CrCl₂ / 0 °C

11: 1) n-Bu₄NF; 2) NaH / 1) THF

With pyridine; 1H-imidazole; chromium dichloride; sodium hydroxide; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; camphor-10-sulfonic acid; borane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; p-toluenesulfonyl chloride; palladium on activated charcoal; nickel; In methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4039(00)84872-8

upstream raw materials:

(2S,3R)-2-{(2S,3R,5R,6S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-6-isopropoxy-5-methyl-tetrahydro-pyran-2-yl}-hex-5-en-3-ol

4-chloromethyl-1,2-dimethoxy-benzene

5(R)-<5(R)-(2-hydroxyethyl)-2(S)-isopropyloxy-3(R)-methyl-6(S)-tetrahydropyranyl>-4(R)-hydroxy-1-hexane

3-deoxy-3-C-<(ethoxycarbonyl)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

Downstream raw materials:

(2S,3R,5R,6S)-5-[2-(3,4-Dimethoxy-benzyloxy)-ethyl]-6-((1S,2R)-2-hydroxy-1-methyl-pent-4-enyl)-3-methyl-tetrahydro-pyran-2-ol

(4R,5S,6S,7R,9R)-7-<2-(3,4-dimethoxybenzyloxy)ethyl>-5,9-dimethyl-4,6-isopropylidenedioxy-1-decen-10-ol

(4R,5S,6S,7R,9R)-7-<2-(3,4-dimethoxybenzyloxy)ethyl>-5,9-dimethyl-4,6,10-trihydroxy-1-decene

(2R,4R,5S,6S,7R)-4-<2-(3,4-dimethoxybenzyloxy)ethyl>-2,6-dimethyl-5,7-isopropylidenedioxy-9-decenal

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