[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

Base Information

Chemical Name:[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile
CAS No.:629645-80-3
Molecular Formula:C₃₄H₄₉NO₅Si
Molecular Weight:579.852
Hs Code.:

[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

Synonyms:[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

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Chemical Property of [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

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Technology Process of [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

There total 13 articles about [(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile 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: 100.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 630102-85-1
[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

: 629645-80-3
[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;
DOI:10.1016/j.tetlet.2003.09.003

Reference yield:

: 131310-61-7
(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 629645-80-3
[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 13 steps

1.1: O₃ / methanol / -78 °C

1.2: Me₂S / methanol

2.1: Zn powder; satd. NH₄Cl / tetrahydrofuran / 0 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: PPh₃ / CH₂Cl₂

4.1: pyridine; DMAP / CH₂Cl₂ / Heating

5.1: 65 percent / BF₃*OEt₂ / acetonitrile / 0 °C

6.1: 98 percent / NaOMe / methanol / 20 °C

7.1: 100 percent / KH / tetrahydrofuran / 20 °C

8.1: 9-BBN / tetrahydrofuran / 20 °C

8.2: 96 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 0 °C

9.1: KH / tetrahydrofuran / 20 °C

10.1: CSA / methanol / 20 °C

11.1: 89 percent / Et₃N / CH₂Cl₂ / Heating

12.1: 100 percent / DMSO / 50 °C

13.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; potassium hydride; ammonium chloride; ozone; dimethyl sulfoxide; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2.1: Barbier allylation;
DOI:10.1016/j.tetlet.2003.09.003

Reference yield:

: 100-39-0
benzyl bromide

: 629645-80-3
[(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-3-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / KH / tetrahydrofuran / 20 °C

2.1: 9-BBN / tetrahydrofuran / 20 °C

2.2: 96 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 0 °C

3.1: KH / tetrahydrofuran / 20 °C

4.1: CSA / methanol / 20 °C

5.1: 89 percent / Et₃N / CH₂Cl₂ / Heating

6.1: 100 percent / DMSO / 50 °C

7.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tetlet.2003.09.003