(S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol

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Chemical Name:(S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol
CAS No.:126393-92-8
Molecular Formula:C₂₃H₃₆O₆
Molecular Weight:408.535
Hs Code.:

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Chemical Property of (S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol

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Technology Process of (S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol

There total 18 articles about (S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol 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:

: 96823-48-2
(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

: 126393-92-8
(S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol

Guidance literature:: Multi-step reaction with 18 steps

1: 1) NaH / 1) THF, DMSO, RT, 2) THF, DMSO, RT, overnight

2: 81 percent / 1N HCl / tetrahydrofuran / 7.5 h / 45 °C

3: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: K₂CO₃ / methanol / 0.5 h / Ambient temperature

5: 90 percent / DDQ / H₂O; CH₂Cl₂ / 0.33 h / 0 °C

6: 90 percent / CSA / CH₂Cl₂ / 0.25 h / 0 °C

7: 96 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0.5 h / Ambient temperature

8: hydrogen / Pd/C / ethanol / 72 h / Ambient temperature

9: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

10: 72 percent / pyridinium chlorochromate, mol. sieves 3A / CH₂Cl₂ / 0.67 h / Ambient temperature

11: 100 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

12: 83 percent / CSA / CH₂Cl₂ / 3 h / Ambient temperature

13: 1) NaH / 1) THF, DMSO, 2) THF, DMSO, RT

14: 1N HCl / methanol / 0.33 h / Ambient temperature

15: 1) DMSO, (COCl)2,2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

16: 95 percent / CH₂Cl₂ / 2.5 h / Heating

17: 96 percent / DIBAH / CH₂Cl₂ / 0.67 h / -78 °C

18: 1) diethyl (+)-L-tartrate, Ti(OiPr)4, 2) t-BuOOH / 1) CH₂Cl₂, -23 deg C, 2) CH₂Cl₂, toluene, -20 deg C, 2 d

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;
DOI:10.1248/cpb.37.1705

Reference yield:

: 96823-41-5
(5S,6R,9R,10S)-9-Benzyloxy-10-(3,4-dimethoxy-benzyloxy)-9-ethyl-5-methyl-undec-1-ene-5,6-diol

: 126393-92-8
(S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol

Guidance literature:: Multi-step reaction with 16 steps

1: Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: K₂CO₃ / methanol / 0.5 h / Ambient temperature

3: 90 percent / DDQ / H₂O; CH₂Cl₂ / 0.33 h / 0 °C

4: 90 percent / CSA / CH₂Cl₂ / 0.25 h / 0 °C

5: 96 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0.5 h / Ambient temperature

6: hydrogen / Pd/C / ethanol / 72 h / Ambient temperature

7: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

8: 72 percent / pyridinium chlorochromate, mol. sieves 3A / CH₂Cl₂ / 0.67 h / Ambient temperature

9: 100 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

10: 83 percent / CSA / CH₂Cl₂ / 3 h / Ambient temperature

11: 1) NaH / 1) THF, DMSO, 2) THF, DMSO, RT

12: 1N HCl / methanol / 0.33 h / Ambient temperature

13: 1) DMSO, (COCl)2,2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

14: 95 percent / CH₂Cl₂ / 2.5 h / Heating

15: 96 percent / DIBAH / CH₂Cl₂ / 0.67 h / -78 °C

16: 1) diethyl (+)-L-tartrate, Ti(OiPr)4, 2) t-BuOOH / 1) CH₂Cl₂, -23 deg C, 2) CH₂Cl₂, toluene, -20 deg C, 2 d

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;
DOI:10.1248/cpb.37.1705

Reference yield:

: 96823-49-3
(5S,6R,9R,10S)-9-benzyloxy-9-ethyl-10-(3,4-dimethoxybenzyloxy)-5,6-<1-(4-methoxyphenyl)ethylidenedioxy>-5-methylundec-1-ene

: 126393-92-8
(S)-1-<(2R,5S)-5-<(2R,5R,6S)-5-ethyl-5-(4-methoxybenzyloxy)-6-methyltetrahydropyran-2-yl>-5-methyltetrahydrofuran-2-yl>ethane-1,2-diol

Guidance literature:: Multi-step reaction with 17 steps

1: 81 percent / 1N HCl / tetrahydrofuran / 7.5 h / 45 °C

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: K₂CO₃ / methanol / 0.5 h / Ambient temperature

4: 90 percent / DDQ / H₂O; CH₂Cl₂ / 0.33 h / 0 °C

5: 90 percent / CSA / CH₂Cl₂ / 0.25 h / 0 °C

6: 96 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0.5 h / Ambient temperature

7: hydrogen / Pd/C / ethanol / 72 h / Ambient temperature

8: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

9: 72 percent / pyridinium chlorochromate, mol. sieves 3A / CH₂Cl₂ / 0.67 h / Ambient temperature

10: 100 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Ambient temperature

11: 83 percent / CSA / CH₂Cl₂ / 3 h / Ambient temperature

12: 1) NaH / 1) THF, DMSO, 2) THF, DMSO, RT

13: 1N HCl / methanol / 0.33 h / Ambient temperature

14: 1) DMSO, (COCl)2,2) Et₃N / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, -70 to 0 deg C

15: 95 percent / CH₂Cl₂ / 2.5 h / Heating

16: 96 percent / DIBAH / CH₂Cl₂ / 0.67 h / -78 °C

17: 1) diethyl (+)-L-tartrate, Ti(OiPr)4, 2) t-BuOOH / 1) CH₂Cl₂, -23 deg C, 2) CH₂Cl₂, toluene, -20 deg C, 2 d

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; 3 A molecular sieve; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;
DOI:10.1248/cpb.37.1705