tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]carbamate

Base Information

• Chemical Name: tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]carbamate
• CAS No.: 1414099-55-0
• Molecular Formula: C₂₂H₃₁NO₆
• Molecular Weight: 405.491

Synonyms:tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]carbamate

Chemical Property of tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]carbamate

There total 6 articles about tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]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: 79.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]allyl]-1,3-isoindolinedione (1414099-50-5) → tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]carbamate (1414099-55-0)

Guidance literature:

2-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]allyl]-1,3-isoindolinedione; With hydrazine hydrate; In methanol; at 20 ℃; for 5h;

di-tert-butyl dicarbonate; In methanol; at 0 - 20 ℃; for 6h;

DOI:10.1039/c2ob26615f

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]carbamate (1414099-55-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C

2.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 3 h / -78 °C

2.2: 0.5 h / -78 °C

3.1: potassium tert-butylate / tetrahydrofuran / 5 h / -10 °C

3.2: 12 h / 20 °C

4.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

5.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 6 h / 0 - 20 °C

6.1: hydrazine hydrate / methanol / 5 h / 20 °C

6.2: 6 h / 0 - 20 °C

With oxalyl dichloride; di-isopropyl azodicarboxylate; potassium tert-butylate; toluene-4-sulfonic acid; hydrazine hydrate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1039/c2ob26615f

Reference yield:

C21H28O7 (1414099-34-5) → tert-butyl N-[2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl perhydrofuro[2,3-d]-[1,3]dioxol-5-yl]allyl]carbamate (1414099-55-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / tetrahydrofuran / 5 h / -10 °C

1.2: 12 h / 20 °C

2.1: toluene-4-sulfonic acid / methanol / 2 h / 20 °C

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 6 h / 0 - 20 °C

4.1: hydrazine hydrate / methanol / 5 h / 20 °C

4.2: 6 h / 0 - 20 °C

With di-isopropyl azodicarboxylate; potassium tert-butylate; toluene-4-sulfonic acid; hydrazine hydrate; triphenylphosphine; In tetrahydrofuran; methanol;

DOI:10.1039/c2ob26615f

upstream raw materials:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

(1R)-1-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(tetrahydro-2H-2-pyranyloxy)ethan-1-ol

C₂₁H₂₈O₇

(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyl-5-1-[(tetrahydro-2H-2-pyranyloxy)methyl]vinylperhydrofuro[2,3-d][1,3]dioxole

Downstream raw materials:

tert-butyl N-[2(S)-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropyl]carbamate

tert-butyl N-[2(R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropyl]carbamate

tert-butyl N-[2(S)-2-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropyl]carbamate

tert-butyl N-[2(S)-2-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethylperhydrofuro[2,3-d]-[1,3]dioxol-5-yl]-3-methoxypropyl]carbamate

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