(2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol

Base Information

Chemical Name:(2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol
CAS No.:342902-10-7
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

Synonyms:(2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol

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Chemical Property of (2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol

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Technology Process of (2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol

There total 6 articles about (2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol 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: 68.0%

: 342901-94-4
(3S,4S,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-3,4,7-trimethyl-hexahydro-pyrano[3,2-b]pyran-2-one

: 1730-25-2
allylmagnesium bromide

: 342902-10-7
(2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

: 157219-94-8
(3R,3aR,5S,6S,7S,7aS)-7-Benzyloxy-5-methoxy-3,6-dimethyl-hexahydro-furo[3,2-b]pyran-2-one

: 342902-10-7
(2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: DIABLH / CH₂Cl₂ / -78 °C

1.2: NaBH₄ / methanol / 0 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

3.1: dimethylsulfoxide / 70 °C

3.2: Mg / methanol / 20 °C

3.3: 83 percent / imidazole / dimethylformamide / 20 °C

4.1: DIABLH / CH₂Cl₂ / -78 °C

4.2: AcOH / tetrahydrofuran; H₂O / 20 °C

4.3: 78 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

5.1: 82 percent / LiHMDS / tetrahydrofuran / -78 °C

6.1: 68 percent / tetrahydrofuran / -78 °C

With dmap; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 6.1: Grignard reaction;
DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

: (2R,3S,4S,5S,6S)-4-Benzyloxy-2-((S)-2-hydroxy-1-methyl-ethyl)-6-methoxy-5-methyl-tetrahydro-pyran-3-ol

: 342902-10-7
(2R,3S,4S,4aR,6S,7S,8S,8aS)-2-Allyl-8-benzyloxy-6-methoxy-3,4,7-trimethyl-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

2.1: dimethylsulfoxide / 70 °C

2.2: Mg / methanol / 20 °C

2.3: 83 percent / imidazole / dimethylformamide / 20 °C

3.1: DIABLH / CH₂Cl₂ / -78 °C

3.2: AcOH / tetrahydrofuran; H₂O / 20 °C

3.3: 78 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

4.1: 82 percent / LiHMDS / tetrahydrofuran / -78 °C

5.1: 68 percent / tetrahydrofuran / -78 °C

With dmap; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 5.1: Grignard reaction;
DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W