<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate

Base Information

Chemical Name:<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate
CAS No.:139426-85-0
Molecular Formula:C₃₀H₅₂O₇Si
Molecular Weight:552.824
Hs Code.:

Synonyms:<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate

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Chemical Property of <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate

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Technology Process of <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate

There total 15 articles about <3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate 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:

: 139426-79-2
<4S,3(2S)>-4-benzyl-3-(2-hydroxy-3,3,4-trimethyl-4-pentenoyl)-2-oxazolidinone

: 139426-85-0
<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, 25 deg C, 30 min, 2.) CH₂Cl₂, toluene, reflux, 24 h

2: 1.) NaH / 1.) DMF, THF, 15 min, 2.) DMF, THF, 5 min

3: 93 percent / DIBAL-H / toluene / -78 °C

4: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

5: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: 1.) tris(triphenylphosphine)rhodium(I) chloride, catecholborane, 2.) 2M NaOH, 30percent aq. H₂O₂ / 1.) THF, 50 min, 2.) THF, EtOH, a) 0 deg C, 30 min, b) from 0 deg C to RT, 30 min

7: 89 percent / DMAP, pyridine / CH₂Cl₂

8: 1.) N-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 h, 2.) t-BuOH, THF, H₂O, 20 h

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; dihydrogen peroxide; trimethylaluminum; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; magnesium bromide; benzo[1,3,2]dioxaborole; In dichloromethane; toluene;
DOI:10.1021/ja00050a024

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 139426-85-0
<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 1.) tris(triphenylphosphine)rhodium(I) chloride, catecholborane, 2.) 2M NaOH, 30percent aq. H₂O₂ / 1.) THF, 50 min, 2.) THF, EtOH, a) 0 deg C, 30 min, b) from 0 deg C to RT, 30 min

3: 89 percent / DMAP, pyridine / CH₂Cl₂

4: 1.) N-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 h, 2.) t-BuOH, THF, H₂O, 20 h

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; dihydrogen peroxide; 4-methylmorpholine N-oxide; benzo[1,3,2]dioxaborole; In dichloromethane;
DOI:10.1021/ja00050a024

Reference yield:

: 139427-03-5
<2S>-2-hydroxy-N-methoxy-N,3,3,4-tetramethyl-4-pentenamide

: 139426-85-0
<3R,4S,5S>-3-methoxy-5-<(p-methoxybenzyl)oxy>-6,6-dimethyl-7-oxo-4-(triethylsiloxy)octyl pivalate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DMF, THF, 15 min, 2.) DMF, THF, 5 min

2: 93 percent / DIBAL-H / toluene / -78 °C

3: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

4: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 1.) tris(triphenylphosphine)rhodium(I) chloride, catecholborane, 2.) 2M NaOH, 30percent aq. H₂O₂ / 1.) THF, 50 min, 2.) THF, EtOH, a) 0 deg C, 30 min, b) from 0 deg C to RT, 30 min

6: 89 percent / DMAP, pyridine / CH₂Cl₂

7: 1.) N-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 h, 2.) t-BuOH, THF, H₂O, 20 h

With pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; magnesium bromide; benzo[1,3,2]dioxaborole; In dichloromethane; toluene;
DOI:10.1021/ja00050a024