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

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yl ester
CAS No.:552890-31-0
Molecular Formula:C₂₄H₃₆O₇
Molecular Weight:436.546
Hs Code.:

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

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

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

There total 9 articles about 2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-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: 97.0%

: 3282-30-2
pivaloyl chloride

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

: 552890-31-0
2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

: 15354-29-7
methyl 4,6-O-isopropylidene-α-D-glucopyranoside

: 552890-31-0
2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 68 percent / pyridine / CH₂Cl₂ / 48 h / 20 °C

2.1: CHCl₃; toluene / 1 h / 20 °C

2.2: toluene; CHCl₃ / 48 h / Heating

3.1: 5.32 g / NaH₂PO₂*H₂O; AIBN / 2-methoxy-ethanol / Heating

4.1: 93 percent / NaOMe / methanol; tetrahydrofuran / 0.75 h / 20 °C

5.1: KOH / 1 h / 110 °C

6.1: 32.0 g / Am,berlyst 15E(R) / methanol / 0.67 h / 20 °C

7.1: 97 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; potassium hydroxide; sodium hypophosphite; 2,2'-azobis(isobutyronitrile); Am,berlyst 15E(R); sodium methylate; isobutyric Acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; 2-methoxy-ethanol; toluene;
DOI:10.1016/S0040-4020(03)00873-1

Reference yield:

: 552890-29-6
2,2-Dimethyl-propionic acid (4aR,6S,7R,8aS)-6-methoxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

: 552890-31-0
2,2-Dimethyl-propionic acid (2R,3S,5R,6S)-5-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / NaOMe / methanol; tetrahydrofuran / 0.75 h / 20 °C

2: KOH / 1 h / 110 °C

3: 32.0 g / Am,berlyst 15E(R) / methanol / 0.67 h / 20 °C

4: 97 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

With dmap; potassium hydroxide; Am,berlyst 15E(R); sodium methylate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/S0040-4020(03)00873-1