((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester

Base Information

• Chemical Name: ((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester
• CAS No.: 357271-86-4
• Molecular Formula: C₁₉H₂₇NO₇
• Molecular Weight: 381.426
• Mol file: 357271-86-4.mol

Synonyms:((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester

Chemical Property of ((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester

There total 5 articles about ((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl 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:

benzyl chloroformate (501-53-1,94274-21-2) + ((3aR,4R,6R,7R,7aR)-4-Methoxy-2,2-dimethyl-7-methylamino-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol (357271-85-3) → ((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester (357271-86-4)

Guidance literature:

With potassium carbonate; In 1,4-dioxane; water; at 23 ℃; for 10h;

DOI:10.1021/ol010119s

Reference yield:

(3aR,4R,6S,7S,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol → ((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester (357271-86-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 98.7 percent / Et₃N / 168 h / 23 °C

2: 85 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

3: 0.266 g / KH; 18-crown-6 / tetrahydrofuran / 4 h / -30 °C

4: NaOH / H₂O / 4 h / Heating

5: 542 mg / K₂CO₃ / dioxane; H₂O / 10 h / 23 °C

With pyridine; sodium hydroxide; 18-crown-6 ether; potassium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1021/ol010119s

Reference yield:

(3aR,4R,5aR,9aR,9bR)-4-Methoxy-2,2,9-trimethyl-hexahydro-1,3,5,7-tetraoxa-9-aza-cyclopenta[a]naphthalen-8-one (357271-76-2) → ((3aR,4R,6R,7R,7aR)-6-Hydroxymethyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester (357271-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH / H₂O / 4 h / Heating

2: 542 mg / K₂CO₃ / dioxane; H₂O / 10 h / 23 °C

With sodium hydroxide; potassium carbonate; In 1,4-dioxane; water;

DOI:10.1021/ol010119s

upstream raw materials:

benzyl chloroformate

((3aR,4R,6R,7R,7aR)-4-Methoxy-2,2-dimethyl-7-methylamino-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

(3aR,4R,5aR,9aR,9bR)-4-Methoxy-2,2,9-trimethyl-hexahydro-1,3,5,7-tetraoxa-9-aza-cyclopenta[a]naphthalen-8-one

Methyl-carbamic acid (3aR,4R,6S,7S,7aR)-7-hydroxy-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl ester

Downstream raw materials:

(3aR,4R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

(3aR,4R,6R,7S,7aR)-7-(Benzyloxycarbonyl-methyl-amino)-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylic acid methyl ester

((3aR,4R,6R,7S,7aR)-6-Formyl-4-methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-methyl-carbamic acid benzyl ester