2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester
CAS No.:186414-27-7
Molecular Formula:C₃₂H₄₃NO₁₀S
Molecular Weight:633.76
Hs Code.:

2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester

There total 8 articles about 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-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:

: 76520-93-9
methyl 2,3-di-O-pivaloyl-α-D-glucopyranoside

: 186414-27-7
2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / pyridine / 24 h / Ambient temperature

2: 90 percent / NaN₃ / dimethylformamide / 10 h / 80 - 85 °C

3: 93 percent / H₂ / 10percent Pd/C / ethanol

4: 80 percent / K₂CO₃ / H₂O; CH₂Cl₂ / 7 h / Ambient temperature

5: 59 percent / TsOH / benzene / 20 h / Heating

6: L-Selectride / tetrahydrofuran / -78 °C / varying reagents temp., solvents

With pyridine; sodium azide; hydrogen; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(96)02311-8

Reference yield:

: 76520-90-6,112317-67-6
methyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside

: 186414-27-7
2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / 5percent HCl / methanol / Heating

2: 86 percent / pyridine / 24 h / Ambient temperature

3: 90 percent / NaN₃ / dimethylformamide / 10 h / 80 - 85 °C

4: 93 percent / H₂ / 10percent Pd/C / ethanol

5: 80 percent / K₂CO₃ / H₂O; CH₂Cl₂ / 7 h / Ambient temperature

6: 59 percent / TsOH / benzene / 20 h / Heating

7: L-Selectride / tetrahydrofuran / -78 °C / varying reagents temp., solvents

With pyridine; hydrogenchloride; sodium azide; hydrogen; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(96)02311-8

Reference yield:

: 2,2-Dimethyl-propionic acid (2R,3R,4S,5R,6S)-2-azidomethyl-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester

: 186414-27-7
2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 93 percent / H₂ / 10percent Pd/C / ethanol

2: 80 percent / K₂CO₃ / H₂O; CH₂Cl₂ / 7 h / Ambient temperature

3: 59 percent / TsOH / benzene / 20 h / Heating

4: L-Selectride / tetrahydrofuran / -78 °C / varying reagents temp., solvents

With hydrogen; L-Selectride; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; benzene;
DOI:10.1016/S0040-4039(96)02311-8