(3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone

Base Information

Chemical Name:(3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone
CAS No.:141276-83-7
Molecular Formula:C₂₇H₅₆O₉Si₂
Molecular Weight:580.907
Hs Code.:

(3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone

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Chemical Property of (3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone

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Technology Process of (3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone

There total 15 articles about (3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone 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:

: 994-30-9
triethylsilyl chloride

: 141276-83-7
(3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone

Guidance literature:: Multi-step reaction with 10 steps

1: 97 percent / pyridine / 60 °C

2: 87 percent / MeONa / methanol / Ambient temperature

3: pyridinium chlorochromate (PCC) / CH₂Cl₂

4: 68 percent / potassium hexamethyldisilazane, 18-crown-6 / tetrahydrofuran / -78 °C

5: (i-Bu)2AlH / CH₂Cl₂ / -78 °C

6: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature

7: 44 percent / OsO₄, N-methylmorpholine N-oxide (NMO) / acetone; H₂O / Ambient temperature

8: 100 percent / N,N-(i-Pr)2EtN / CH₂Cl₂ / Heating

9: H₂ / 10percent Pd/C / ethanol

10: pyridinium chlorochromate (PCC) / CH₂Cl₂

With pyridine; dmap; osmium(VIII) oxide; potassium hexamethyldisilazane; 18-crown-6 ether; hydrogen; sodium methylate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone;
DOI:10.1039/c39920000406

Reference yield:

: (1R,2S,4R,6S)-2-Hydroxymethyl-6-methoxymethoxy-cyclohexane-1,4-diol

: 141276-83-7
(3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone

Guidance literature:: Multi-step reaction with 14 steps

1: dimethylformamide

2: NaH / dimethylformamide / Ambient temperature

3: AcOH, H₂O / Ambient temperature

4: pyridine

5: 97 percent / pyridine / 60 °C

6: 87 percent / MeONa / methanol / Ambient temperature

7: pyridinium chlorochromate (PCC) / CH₂Cl₂

8: 68 percent / potassium hexamethyldisilazane, 18-crown-6 / tetrahydrofuran / -78 °C

9: (i-Bu)2AlH / CH₂Cl₂ / -78 °C

10: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature

11: 44 percent / OsO₄, N-methylmorpholine N-oxide (NMO) / acetone; H₂O / Ambient temperature

12: 100 percent / N,N-(i-Pr)2EtN / CH₂Cl₂ / Heating

13: H₂ / 10percent Pd/C / ethanol

14: pyridinium chlorochromate (PCC) / CH₂Cl₂

With pyridine; dmap; osmium(VIII) oxide; potassium hexamethyldisilazane; 18-crown-6 ether; water; hydrogen; sodium methylate; sodium hydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1039/c39920000406

Reference yield:

: (4aS,6R,8S,8aR)-8-Methoxymethoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxin-6-ol

: 141276-83-7
(3S,4R,5R)-5-<(1S,2R)-3-(tert-butyldimethylsilyloxy)-1,2-bis(methoxymethoxy)propyl>-3-methoxymethoxy-4-triethylsilyloxy-1-cyclohexanone

Guidance literature:: Multi-step reaction with 13 steps

1: NaH / dimethylformamide / Ambient temperature

2: AcOH, H₂O / Ambient temperature

3: pyridine

4: 97 percent / pyridine / 60 °C

5: 87 percent / MeONa / methanol / Ambient temperature

6: pyridinium chlorochromate (PCC) / CH₂Cl₂

7: 68 percent / potassium hexamethyldisilazane, 18-crown-6 / tetrahydrofuran / -78 °C

8: (i-Bu)2AlH / CH₂Cl₂ / -78 °C

9: 97 percent / 4-(N,N-dimethylamino)pyridine, Et₃N / CH₂Cl₂ / Ambient temperature

10: 44 percent / OsO₄, N-methylmorpholine N-oxide (NMO) / acetone; H₂O / Ambient temperature

11: 100 percent / N,N-(i-Pr)2EtN / CH₂Cl₂ / Heating

12: H₂ / 10percent Pd/C / ethanol

13: pyridinium chlorochromate (PCC) / CH₂Cl₂

With pyridine; dmap; osmium(VIII) oxide; potassium hexamethyldisilazane; 18-crown-6 ether; water; hydrogen; sodium methylate; sodium hydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1039/c39920000406