(-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate

Base Information

Chemical Name:(-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate
CAS No.:880766-50-7
Molecular Formula:C₃₄H₄₄O₇Si
Molecular Weight:592.805
Hs Code.:

Synonyms:(-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate

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Chemical Property of (-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate

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Technology Process of (-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate

There total 13 articles about (-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate 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:

: 31469-15-5
1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

: 289666-91-7
(2S,3R,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanal

: 880766-50-7
(-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate

: (-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-4,6-methylenedioxy-3-trimethylsilyloxyheptanoate

: 289666-93-9
(-)-methyl (3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate

: 289666-92-8
(+)-methyl (3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-4,6-methylenedioxy-3-trimethylsilyloxyheptanoate

Guidance literature:: With chloro-trimethyl-silane; ytterbium(III) triflate; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol052943c

Reference yield:

: (2RS,3R,4R)-3-benzyloxy-4,5-isopropylidenedioxy-1,2-pentanediol

: 880766-50-7
(-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate

Guidance literature:: Multi-step reaction with 7 steps

1: 61 percent / DMAP; Et₃N / CH₂Cl₂ / 10 h / 20 °C

2: 98 percent / AcOH; H₂O / tetrahydrofuran / 6 h / 55 °C

3: 89 percent / pyridine / CH₂Cl₂ / 10 h / 20 °C

4: 88 percent / P₂O₅ / CH₂Cl₂ / 1.5 h

5: 99 percent / DIBALH / tetrahydrofuran / 1 h / 0 °C

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

7: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

With pyridine; dmap; oxalyl dichloride; water; phosphorus pentoxide; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; 6: Swern oxidation;
DOI:10.1021/jo060803q

Reference yield:

: 289666-90-6
(+)-(2R,3S,4R)-3-benzyloxy-1-tert-butyldiphenylsilyloxy-2,4-methylenedioxypentanol

: 880766-50-7
(-)-methyl (3S,4R,5R,6S)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-hydroxy-4,6-methylenedioxy-heptanoate

Guidance literature:: Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -30 °C

2: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In dichloromethane; 1: Swern oxidation;
DOI:10.1021/jo060803q