[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol

Base Information

Chemical Name:[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol
CAS No.:440333-74-4
Molecular Formula:C₄₆H₆₂O₉Si
Molecular Weight:787.078
Hs Code.:

[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol

Synonyms:[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol

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Chemical Property of [(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol

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Technology Process of [(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol

There total 12 articles about [(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol 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: 77.0%

: Trimethyl-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-stannane

: 440333-67-5
(2S,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepane-2-carbaldehyde

: 440333-74-4
[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol

Guidance literature:: Trimethyl-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-stannane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

(2S,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepane-2-carbaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: (2R,4aR,6S,7R,8aS)-4a-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 440333-74-4
[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol

Guidance literature:: Multi-step reaction with 12 steps

1.1: O₃ / methanol / -78 °C

1.2: 78 percent / NaBH₄ / methanol / -78 - 20 °C

2.1: 86 percent / imidazole / dimethylformamide / 20 °C

3.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

3.2: 93 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: BF₃*OEt₂ / CH₂Cl₂ / -78 °C

4.2: 74 percent / PPTS / methanol / 20 °C

5.1: 89 percent / TBAF / tetrahydrofuran / 20 °C

6.1: 89 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -20 °C

7.1: 68 percent / KH / tetrahydrofuran / 0 - 20 °C

8.1: 86 percent / aq. HCl / methanol / 20 °C

9.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

10.1: 89 percent / camphorsulfonic acid / methanol / 0 °C

11.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

11.2: 93 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

12.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

12.2: 77 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; ozone; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; 3.1: Swern oxidation / 11.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 440333-93-7
(2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 440333-74-4
[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-((2R,4aR,5aS,9aR,11aS)-2-phenyl-4,4a,5a,6,9a,10,11,11a-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-8-yl)-methanol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 86 percent / imidazole / dimethylformamide / 20 °C

2.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

2.2: 93 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: BF₃*OEt₂ / CH₂Cl₂ / -78 °C

3.2: 74 percent / PPTS / methanol / 20 °C

4.1: 89 percent / TBAF / tetrahydrofuran / 20 °C

5.1: 89 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -20 °C

6.1: 68 percent / KH / tetrahydrofuran / 0 - 20 °C

7.1: 86 percent / aq. HCl / methanol / 20 °C

8.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

9.1: 89 percent / camphorsulfonic acid / methanol / 0 °C

10.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

10.2: 93 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

11.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

11.2: 77 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; 2.1: Swern oxidation / 10.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00039-X