dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate

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Chemical Name:dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate
CAS No.:152838-18-1
Molecular Formula:C₃₉H₄₉O₇PSi
Molecular Weight:688.873
Hs Code.:

Synonyms:dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate

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Chemical Property of dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate

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Technology Process of dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate

There total 12 articles about dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate 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: 90.0%

: 152838-17-0
methyl (2R,4R)-dibenzyloxy-6-tert-butyldiphenylsilyloxy-hexanoate

: 756-79-6
dimethyl methane phosphonate

: 152838-18-1
dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 3h; 1.) 30 min;
DOI:10.1016/S0040-4020(01)96261-1

Reference yield:

: 3150-16-1
methyl 4,6-O-benzylidene-2,3-anhydro-α-D-mannopyranoside

: 152838-18-1
dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / LiAlH₄ / diethyl ether / 12 h / Heating

2: 1.) oxalyl chloride, DMSO, NEt₃, 2.) NaBH₄ / 1.) CH₂Cl₂, -70 deg C to room temperature, 2.) CH₂Cl₂, water, 2 h

3: 95 percent / 1.) KH / tetrahydrofuran / 0.5 h / Ambient temperature; 1.) 30 min 0 deg C to room temperature

4: 66 percent / BH₃*NMe₃/AlCl₃, molecular sieves 4Angstroem / toluene / 0.17 h / Ambient temperature

5: 88 percent / imidazole, PPh₃, iodine / toluene / 4 h / Ambient temperature

6: 86 percent / Zn/Ag-graphite / tetrahydrofuran / 0.17 h / Ambient temperature

7: 97 percent / p-toluenesulfonic acid monohydrate / methanol / 0.25 h / Ambient temperature

8: 1.) 9-BBN dimer, 2.) 3N NaOH, 30percent H₂O₂ / 1.) THF, 3 h, room temperature, 2.) THF, water, 0 deg C, 30 min

9: 86 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

10: 95 percent / p-toluenesulfonic acid monohydrate / acetone / 6 h

11: 68 percent / PCC / dimethylformamide / 48 h / Ambient temperature

12: 90 percent / 1.) n-BuLi (1.6M in hexane) / tetrahydrofuran / 3 h / -78 °C / 1.) 30 min

With 1H-imidazole; sodium hydroxide; sodium tetrahydroborate; silver-graphite; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; trimethylamine-borane; 4 A molecular sieve; dihydrogen peroxide; iodine; potassium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; pyridinium chlorochromate; zinc; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4020(01)96261-1

Reference yield:

: 40773-64-6
methyl 4,6-O-benzylidene-3-deoxy-ribo-hexopyranoside

: 152838-18-1
dimethyl <(3R,5R)-dibenzyloxy-7-tert-butyldiphenylsilyloxy-heptan-2-on-1-yl> phosphonate

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / 1.) KH / tetrahydrofuran / 0.5 h / Ambient temperature; 1.) 30 min 0 deg C to room temperature

2: 66 percent / BH₃*NMe₃/AlCl₃, molecular sieves 4Angstroem / toluene / 0.17 h / Ambient temperature

3: 88 percent / imidazole, PPh₃, iodine / toluene / 4 h / Ambient temperature

4: 86 percent / Zn/Ag-graphite / tetrahydrofuran / 0.17 h / Ambient temperature

5: 97 percent / p-toluenesulfonic acid monohydrate / methanol / 0.25 h / Ambient temperature

6: 1.) 9-BBN dimer, 2.) 3N NaOH, 30percent H₂O₂ / 1.) THF, 3 h, room temperature, 2.) THF, water, 0 deg C, 30 min

7: 86 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

8: 95 percent / p-toluenesulfonic acid monohydrate / acetone / 6 h

9: 68 percent / PCC / dimethylformamide / 48 h / Ambient temperature

10: 90 percent / 1.) n-BuLi (1.6M in hexane) / tetrahydrofuran / 3 h / -78 °C / 1.) 30 min

With 1H-imidazole; sodium hydroxide; silver-graphite; n-butyllithium; aluminium trichloride; trimethylamine-borane; 4 A molecular sieve; dihydrogen peroxide; iodine; potassium hydride; toluene-4-sulfonic acid; triphenylphosphine; pyridinium chlorochromate; zinc; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/S0040-4020(01)96261-1