(4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one

Base Information

Chemical Name:(4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one
CAS No.:349552-58-5
Molecular Formula:C₃₀H₃₈O₆
Molecular Weight:494.628
Hs Code.:

Synonyms:(4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one

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Chemical Property of (4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one

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Technology Process of (4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one

There total 13 articles about (4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one 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: 98.0%

: 349552-57-4
(4aS,6R,7S,8S,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-octahydro-1,5-dioxa-benzocyclohepten-7-ol

: 349552-58-5
(4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 23 ℃; for 2h;
DOI:10.1055/s-2001-13387

Reference yield:

: 125877-83-0
(2'S,3'S)-3'-(tert-butyldimethylsiloxy)-tetrahydropyran-2'-carbaldehyde

: 349552-58-5
(4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 2.08 h / -78 - 0 °C

1.2: CH₂Cl₂ / 2.33 h / -78 - -20 °C

2.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.8 h / 25 °C

3.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 2.7 h / 23 °C

4.1: 75 percent / NaH; TBAI / tetrahydrofuran / 20 h / 24 °C

5.1: 93 percent / PPTS / methanol; CH₂Cl₂ / 5 h / 23 °C

6.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.58 h / -78 - 0 °C

7.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

7.2: 96 percent / tetrahydrofuran / 0.42 h / -78 °C

8.1: 29 percent / CuCl₂ / aq. methanol / 20 h / 22 °C

9.1: 97 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

With pyridine; triethylsilane; dmap; sodium tetrahydroborate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; copper dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Evans aldol reaction / 6.1: Swern oxidation;
DOI:10.1055/s-2001-13387

Reference yield:

: 138750-71-7,125877-82-9
(2'R,3'S)-<3'-(tert-butyldimethylsilyloxy)tetrahydropyran-2'-yl>methanol

: 349552-58-5
(4aS,6R,8R,9R,9aS)-9-Benzyloxy-6-((2S,3R)-3-benzyloxy-tetrahydro-pyran-2-ylmethyl)-8-methyl-hexahydro-1,5-dioxa-benzocyclohepten-7-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.55 h / -78 - -18 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 2.08 h / -78 - 0 °C

2.2: CH₂Cl₂ / 2.33 h / -78 - -20 °C

3.1: 100 percent / NaBH₄ / tetrahydrofuran; H₂O / 2.8 h / 25 °C

4.1: 100 percent / DMAP; pyridine / CH₂Cl₂ / 2.7 h / 23 °C

5.1: 75 percent / NaH; TBAI / tetrahydrofuran / 20 h / 24 °C

6.1: 93 percent / PPTS / methanol; CH₂Cl₂ / 5 h / 23 °C

7.1: 100 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.58 h / -78 - 0 °C

8.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

8.2: 96 percent / tetrahydrofuran / 0.42 h / -78 °C

9.1: 29 percent / CuCl₂ / aq. methanol / 20 h / 22 °C

10.1: 97 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

11.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

With pyridine; triethylsilane; dmap; sodium tetrahydroborate; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; copper dichloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; 1.1: Swern oxidation / 2.1: Evans aldol reaction / 7.1: Swern oxidation;
DOI:10.1055/s-2001-13387