(2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol

Base Information

Chemical Name:(2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol
CAS No.:908866-17-1
Molecular Formula:C₂₉H₃₈O₅
Molecular Weight:466.618
Hs Code.:

Synonyms:(2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol

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Chemical Property of (2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol

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Technology Process of (2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol

There total 16 articles about (2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-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: 89.0%

: 908866-15-9
(2R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-octahydro-1,6-dioxa-heptalen-3-one

: 917-54-4
methyllithium

: 908866-17-1
(2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol

: (2R,3S,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 1h;
DOI:10.1021/ja062524q DOI:10.1021/ja066772y

Reference yield:

: 908866-07-9
(2R,3S,6R,7S)-6-Benzyloxy-7-benzyloxymethyl-2-hydroxymethyl-oxepan-3-ol

: 908866-17-1
(2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

1.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

2.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

3.1: OsO₄; aq. 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

3.2: NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

4.1: BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

5.1: 1.39 g / TBAF / tetrahydrofuran / 20 °C

6.1: 1.57 g / 4-methylmorpholine / CH₂Cl₂ / 36 h / 20 °C

7.1: 1.27 g / NaHCO₃; MeI / acetonitrile; H₂O / 35 °C

8.1: SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

8.2: 84 percent / p-TsOH*H₂O / toluene / 1 h / 80 °C

9.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

10.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

10.2: 167.6 mg / tetrahydrofuran / 0.5 h / 0 - 20 °C

11.1: 97 percent / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.83 h / 20 °C

12.1: 89 percent / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; osmium(VIII) oxide; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; copper(I) bromide; methyl iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 6.1: Michael reaction / 10.2: Wittig reaction;
DOI:10.1021/ja066772y

Reference yield:

: (2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

: 908866-17-1
(2R,3R,5aR,7S,8R,10aS)-2-Allyl-8-benzyloxy-7-benzyloxymethyl-3-methyl-decahydro-1,6-dioxa-heptalen-3-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: 9.10 g / CSA / methanol; CHCl₃ / 20 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.2: CH₂Cl₂ / 0.75 h / -78 - 20 °C

3.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C

4.1: OsO₄; aq. 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

4.2: NaIO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

5.1: BF₃*OEt₂ / CH₂Cl₂ / 0.67 h / -78 - 0 °C

6.1: 1.39 g / TBAF / tetrahydrofuran / 20 °C

7.1: 1.57 g / 4-methylmorpholine / CH₂Cl₂ / 36 h / 20 °C

8.1: 1.27 g / NaHCO₃; MeI / acetonitrile; H₂O / 35 °C

9.1: SmI₂; MeOH / tetrahydrofuran / 0.5 h / 20 °C

9.2: 84 percent / p-TsOH*H₂O / toluene / 1 h / 80 °C

10.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

11.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

11.2: 167.6 mg / tetrahydrofuran / 0.5 h / 0 - 20 °C

12.1: 97 percent / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.83 h / 20 °C

13.1: 89 percent / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; osmium(VIII) oxide; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; copper(I) bromide; methyl iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; water; acetonitrile; tert-butyl alcohol; 7.1: Michael reaction / 11.2: Wittig reaction;
DOI:10.1021/ja066772y