[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-acetic acid

Base Information

Chemical Name:[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-acetic acid
CAS No.:440333-59-5
Molecular Formula:C₃₀H₄₄O₆Si
Molecular Weight:528.761
Hs Code.:

Synonyms:[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-acetic acid

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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]-acetic acid

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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]-acetic acid

There total 15 articles about [(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-acetic acid 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:

: [(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-acetaldehyde

: 440333-59-5
[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-acetic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 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

: 440333-59-5
[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-acetic acid

Guidance literature:: Multi-step reaction with 15 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: NaHMDS / tetrahydrofuran / 0 °C

12.2: 33 percent / tetrahydrofuran

13.1: (c-Hex)2BH / tetrahydrofuran / 0 °C

13.2: 93 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran

14.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

15.1: NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium hydride; Dess-Martin periodane; ozone; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 3.1: Swern oxidation / 11.1: Swern oxidation / 12.2: Wittig reaction / 14.1: Dess-Martin 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

: 440333-59-5
[(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-oxepan-2-yl]-acetic acid

Guidance literature:: Multi-step reaction with 14 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: NaHMDS / tetrahydrofuran / 0 °C

11.2: 33 percent / tetrahydrofuran

12.1: (c-Hex)2BH / tetrahydrofuran / 0 °C

12.2: 93 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran

13.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

14.1: NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium hydride; Dess-Martin periodane; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 2.1: Swern oxidation / 10.1: Swern oxidation / 11.2: Wittig reaction / 13.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(02)00039-X