benzyl N-[3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxa bicyclo[3.3.0]oct-4-yl]carbamate

Base Information

• Chemical Name: benzyl N-[3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxa bicyclo[3.3.0]oct-4-yl]carbamate
• CAS No.: 7508-81-8
• Molecular Formula: C20H27 N O7
• Molecular Weight: 0
• Mol file: 7508-81-8.mol

Synonyms:Furo[2,3-d]-1,3-dioxole,a-D-glucofuranose deriv.; NSC407102

Chemical Property of benzyl N-[3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxa bicyclo[3.3.0]oct-4-yl]carbamate

Chemical Property:

• Vapor Pressure: 1.98E-10mmHg at 25°C
• Boiling Point: 507.7°C at 760 mmHg
• Flash Point: 260.9°C
• PSA: 84.48000
• Density: 1.27g/cm³
• LogP: 2.70020

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of benzyl N-[3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxa bicyclo[3.3.0]oct-4-yl]carbamate

There total 7 articles about benzyl N-[3-(2,2-dimethyl-1,3-dioxolan-4-yl)-7,7-dimethyl-2,6,8-trioxa bicyclo[3.3.0]oct-4-yl]carbamate 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:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → [(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester (7508-81-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: NaN₃, 15-crown-5

3: LiAlH₄ / diethyl ether

4: Na₂CO₃

With pyridine; lithium aluminium tetrahydride; sodium azide; 15-crown-5; sodium carbonate; In diethyl ether;

DOI:10.1021/ja9815881

Reference yield:

3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose (13964-23-3) → [(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester (7508-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / diethyl ether

2: Na₂CO₃

With lithium aluminium tetrahydride; sodium carbonate; In diethyl ether;

DOI:10.1021/ja9815881

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → [(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester (7508-81-8)

Guidance literature:

Multi-step reaction with 5 steps

1: NaBH₄ / ethanol

2: pyridine

3: NaN₃, 15-crown-5

4: LiAlH₄ / diethyl ether

5: Na₂CO₃

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; 15-crown-5; sodium carbonate; In diethyl ether; ethanol;

DOI:10.1021/ja9815881

upstream raw materials:

benzyl chloroformate

3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

(1,2:5,6)-di-O-isopropylidene-D-gulose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

Downstream raw materials:

Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-4-benzyloxycarbonylamino-2-(bis-benzyloxy-phosphoryloxy)-6-methyl-tetrahydro-pyran-3-yl ester

Toluene-4-sulfonic acid (R)-2-((3aR,5S,6S,6aR)-6-benzyloxycarbonylamino-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-hydroxy-ethyl ester

Acetic acid (3R,4S,5S,6R)-2,5-diacetoxy-4-benzyloxycarbonylamino-6-methyl-tetrahydro-pyran-3-yl ester

[(3aR,5S,6S,6aR)-5-((S)-1-Hydroxy-2-iodo-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-carbamic acid benzyl ester

Refernces