2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester
CAS No.:552890-35-4
Molecular Formula:C₂₆H₃₈O₆
Molecular Weight:446.584
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 18 articles about 2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester 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:

: 2,2-Dimethyl-propionic acid (2R,3S,5R)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-hydroxy-tetrahydro-pyran-3-yl ester

: 552890-35-4
2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -10 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

: 552890-33-2
2,2-Dimethyl-propionic acid (2R,3S,5R)-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-oxo-tetrahydro-pyran-3-yl ester

: 1730-25-2
allylmagnesium bromide

: 552890-35-4
2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: 2,2-Dimethyl-propionic acid (2R,3S,5R)-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-oxo-tetrahydro-pyran-3-yl ester; allylmagnesium bromide; In tetrahydrofuran; at -78 ℃;

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -10 ℃;
DOI:10.1055/s-2003-37533

Reference yield:

: 50272-15-6
methyl 2-O-benzyl-3,6-dideoxy-α-D-ribo-hexopyranoside

: 552890-35-4
2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-6-allyl-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

2: 87 percent / H₂SO₄ / 0.25 h / 0 °C

3: 66 percent / HCl / 1,2-dimethoxy-ethane; H₂O / 14 h / 55 °C

4: 93 percent / Ac₂O / dimethylsulfoxide / 14 h / 20 °C

5: diethyl ether / 0.5 h / -78 °C

6: 8.02 g / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0.33 h / -10 °C

With hydrogenchloride; triethylsilane; dmap; sulfuric acid; boron trifluoride diethyl etherate; acetic anhydride; In 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1016/S0040-4020(03)00873-1