{(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

Base Information

Chemical Name:{(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane
CAS No.:440333-75-5
Molecular Formula:C₄₆H₆₂O₈Si
Molecular Weight:771.079
Hs Code.:

{(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

Synonyms:{(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

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Chemical Property of {(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

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Technology Process of {(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

There total 13 articles about {(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane 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:

: 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

: [(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-((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-ylmethyl)-oxepan-3-yloxy]-tert-butyl-dimethyl-silane

: 440333-75-5
{(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

Guidance literature:: [(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; With carbon disulfide; potassium hydride; In diethyl ether; at 25 ℃; for 2h;

With methyl iodide; In diethyl ether;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 0.5h;
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

: 440333-75-5
{(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 13 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

13.1: KH; CS₂ / diethyl ether / 2 h / 25 °C

13.2: MeI / diethyl ether

13.3: 3.9 mg / Bu₃SnH; AIBN / benzene / 0.5 h / 80 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; carbon disulfide; 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; diethyl ether; 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

: 440333-75-5
{(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-methyl-2-[(2R,4aR,5aS,9aR,11aS)-2-phenyl-octahydro-1,3,5,9-tetraoxa-dibenzo[a,d]cyclohepten-(8E)-ylidenemethyl]-oxepan-3-yloxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 12 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

12.1: KH; CS₂ / diethyl ether / 2 h / 25 °C

12.2: MeI / diethyl ether

12.3: 3.9 mg / Bu₃SnH; AIBN / benzene / 0.5 h / 80 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; carbon disulfide; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; 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