(6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

Base Information

Chemical Name:(6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose
CAS No.:302788-36-9
Molecular Formula:C₃₃H₃₉NO₅
Molecular Weight:529.676
Hs Code.:

Synonyms:(6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

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Chemical Property of (6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

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Technology Process of (6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

There total 11 articles about (6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose 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: 87.0%

: 302788-34-7
3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydohexos-5-ulo-2,5-furanose N-benzylimine

: 1730-25-2
allylmagnesium bromide

: 302788-36-9
(6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

Guidance literature:: In diethyl ether; at 0 - 20 ℃;
DOI:10.1021/ol0062493

Reference yield: 33.0%

: 302788-34-7
3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydohexos-5-ulo-2,5-furanose N-benzylimine

: 1730-25-2
allylmagnesium bromide

: 302788-36-9
(6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

: (6S)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

Guidance literature:: With boron trifluoride diethyl etherate; In diethyl ether; at -78 - 0 ℃;
DOI:10.1021/jo0203903

Reference yield:

: 17682-70-1
2,3:4,6-bis-O-isopropylidene-L-sorbose

: 302788-36-9
(6R)-6-C-allyl-1,4-di-O-benzyl-6-benzylamino-6-deoxy-2,3-O-isopropylidene-α-L-sorbofuranose

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: 98 percent / tetrabutylammonium bromide / tetrahydrofuran / 3 h / 20 °C

2.1: 99 percent / H₂SO₄ / acetone; H₂O / 3 h / 20 °C

3.1: 95 percent / pyridine / 24 h / 50 °C

4.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

4.2: 99 percent / tetrabutylammonium bromide / tetrahydrofuran / 4 h / 20 °C

5.1: 96 percent / HBr / acetic acid / 10 - 15 °C

6.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 100 percent / molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / 4 °C

8.1: 84 percent / diethyl ether / 0 - 20 °C

With pyridine; 4 A molecular sieve; sulfuric acid; hydrogen bromide; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; acetone;
DOI:10.1021/jo0203903