6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane

Base Information

Chemical Name:6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane
CAS No.:440333-66-4
Molecular Formula:C₃₅H₅₈O₅Si₂
Molecular Weight:615.014
Hs Code.:

6-benzyloxy-7-benzyloxymethyl-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane

Synonyms:6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane

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Chemical Property of 6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane

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Technology Process of 6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane

There total 9 articles about 6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 440333-97-1
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-2-methyl-oxepan-3-ol

: 440333-66-4
6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃;
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

: 440333-66-4
6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; ozone; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; 3.1: 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

: 440333-66-4
6-benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-oxepane

Guidance literature:: Multi-step reaction with 8 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

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