[(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

Base Information

Chemical Name:[(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
CAS No.:630102-85-1
Molecular Formula:C₂₈H₃₅NO₅
Molecular Weight:465.59
Hs Code.:

Synonyms:[(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

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Chemical Property of [(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

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Technology Process of [(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

There total 11 articles about [(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 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%

: 143-33-9,25596-52-5
sodium cyanide

: 630102-84-0
Toluene-4-sulfonic acid (2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-3-hydroxy-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

: 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

Guidance literature:: With dimethyl sulfoxide; at 50 ℃;
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

: 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

Guidance literature:: Multi-step reaction with 12 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

With pyridine; 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:

: (2R,4aR,6R,7R,8aS)-7-Hydroxy-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbaldehyde

: 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

Guidance literature:: Multi-step reaction with 11 steps

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

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: PPh₃ / CH₂Cl₂

3.1: pyridine; DMAP / CH₂Cl₂ / Heating

4.1: 65 percent / BF₃*OEt₂ / acetonitrile / 0 °C

5.1: 98 percent / NaOMe / methanol / 20 °C

6.1: 100 percent / KH / tetrahydrofuran / 20 °C

7.1: 9-BBN / tetrahydrofuran / 20 °C

7.2: 96 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 0 °C

8.1: KH / tetrahydrofuran / 20 °C

9.1: CSA / methanol / 20 °C

10.1: 89 percent / Et₃N / CH₂Cl₂ / Heating

11.1: 100 percent / DMSO / 50 °C

With pyridine; 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; 1.1: Barbier allylation;
DOI:10.1016/j.tetlet.2003.09.003