(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol

Base Information

Chemical Name:(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol
CAS No.:289667-09-0
Molecular Formula:C₃₄H₄₆O₆Si
Molecular Weight:578.821
Hs Code.:

Synonyms:(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol

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Technology Process of (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol

There total 17 articles about (+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol 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: 100.0%

: 289667-10-3
(+)-methyl (3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxy-heptanoate

: 289667-09-0
(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/ol052943c

Reference yield:

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

: 289667-09-0
(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol

Guidance literature:: Multi-step reaction with 4 steps

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

2.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

3.1: NaH / tetrahydrofuran / 0 - 20 °C

3.2: 95 percent / tetrahydrofuran / 0 - 20 °C

4.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

With oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation;
DOI:10.1021/jo060803q

Reference yield:

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

: 289667-09-0
(+)-(3S,4R,5R,6R)-5-benzyloxy-7-tert-butyldiphenylsilyloxy-2,2-dimethyl-3-methoxy-4,6-methylenedioxyheptanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 61 percent / DMAP; Et₃N / CH₂Cl₂ / 10 h / 20 °C

2.1: 98 percent / AcOH; H₂O / tetrahydrofuran / 6 h / 55 °C

3.1: 89 percent / pyridine / CH₂Cl₂ / 10 h / 20 °C

4.1: 88 percent / P₂O₅ / CH₂Cl₂ / 1.5 h

5.1: 99 percent / DIBALH / tetrahydrofuran / 1 h / 0 °C

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

7.1: Yb(OTf)3 / CH₂Cl₂ / 48 h / 20 °C

8.1: NaH / tetrahydrofuran / 0 - 20 °C

8.2: 95 percent / tetrahydrofuran / 0 - 20 °C

9.1: 100 percent / DIBAL-H / tetrahydrofuran / 1 h / 0 °C

With pyridine; dmap; oxalyl dichloride; water; phosphorus pentoxide; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; 6.1: Swern oxidation;
DOI:10.1021/jo060803q