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

Base Information

Chemical Name: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
CAS No.:1414099-60-7
Molecular Formula:C₂₂H₃₃NO₇
Molecular Weight:423.507
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 7 articles about 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 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: 25.0%

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

: 1414099-60-7
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

: 1414099-65-2
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

Guidance literature:: With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 12h; Inert atmosphere;
DOI:10.1039/c2ob26615f

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 1414099-60-7
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

: 1414099-65-2
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

Guidance literature:: Multi-step reaction with 7 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

7.1: dimethylsulfide borane complex / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

With oxalyl dichloride; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; potassium tert-butylate; toluene-4-sulfonic acid; hydrazine hydrate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1039/c2ob26615f

Reference yield:

: 912652-02-9
(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

: 1414099-60-7
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

: 1414099-65-2
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

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 0.5 h / -78 °C

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

2.2: 12 h / 20 °C

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

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

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

5.2: 6 h / 0 - 20 °C

6.1: dimethylsulfide borane complex / tetrahydrofuran / 12 h / 0 - 20 °C / Inert atmosphere

With oxalyl dichloride; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; potassium tert-butylate; toluene-4-sulfonic acid; hydrazine hydrate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1039/c2ob26615f