2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-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)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester
• CAS No.: 186414-21-1
• Molecular Formula: C₃₂H₄₁NO₁₀S
• Molecular Weight: 631.744
• Mol file: 186414-21-1.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-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: 59.0%

phenylglyoxal hydrate (1074-12-0) + 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-3-(2,2-dimethyl-propionyloxy)-5-hydroxy-2-methoxy-6-[(toluene-4-sulfonylamino)-methyl]-tetrahydro-pyran-4-yl ester (186414-19-7) → 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester (186414-21-1) + 2,2-Dimethyl-propionic acid (2S,4aR,6S,7R,8S,8aR)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 20h; Heating;

DOI:10.1016/S0040-4039(96)02311-8

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester (186414-21-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / pyridine

2: 98 percent / 5percent HCl / methanol / Heating

3: 86 percent / pyridine / 24 h / Ambient temperature

4: 90 percent / NaN₃ / dimethylformamide / 10 h / 80 - 85 °C

5: 93 percent / H₂ / 10percent Pd/C / ethanol

6: 80 percent / K₂CO₃ / H₂O; CH₂Cl₂ / 7 h / Ambient temperature

7: 59 percent / TsOH / benzene / 20 h / Heating

With pyridine; hydrogenchloride; sodium azide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(96)02311-8

Reference yield:

methyl 2,3-di-O-pivaloyl-α-D-glucopyranoside (76520-93-9) → 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester (186414-21-1)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; sodium azide; hydrogen; potassium carbonate; toluene-4-sulfonic acid; palladium on activated charcoal; In ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(96)02311-8

upstream raw materials:

phenylglyoxal hydrate

2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-3-(2,2-dimethyl-propionyloxy)-5-hydroxy-2-methoxy-6-[(toluene-4-sulfonylamino)-methyl]-tetrahydro-pyran-4-yl ester

pivaloyl chloride

methyl 2,3-di-O-pivaloyl-α-D-glucopyranoside

Downstream raw materials:

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

(R)-α-acetoxyphenylacetaldehyde

(R)-2-hydroxy-2-phenylacetaldehyde