1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose

Base Information

Chemical Name:1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose
CAS No.:714967-39-2
Molecular Formula:C₂₀H₂₆N₂O₈
Molecular Weight:422.435
Hs Code.:

Synonyms:1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose

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Chemical Property of 1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose

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Technology Process of 1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose

There total 8 articles about 1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose 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: 81.0%

: 1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenyl-carbodiimido)-β-L-gulofuranose

: 714967-39-2
1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose

Guidance literature:: With trifluoroacetic acid; In water; acetone; at 20 ℃; for 8h;
DOI:10.1002/ejoc.200300731

Reference yield:

: 14440-57-4
1-O-acetyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

: 714967-39-2
1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / aq. AcOH / 4 h / 40 °C

2: 84 percent / pyridine / 36 h / 20 °C

3: CH₂Cl₂ / 1 h / -25 °C

4: 1.8 g / NaN₃ / dimethylformamide / 18 h / 20 °C

5: 80 percent / BF₃*Et₂O / methanol; CH₂Cl₂ / 2 h / 0 - 20 °C

6: 85 percent / pyridine

7: 56 percent / TPP / toluene / 18 h / 20 °C

8: 81 percent / TFA / acetone; H₂O / 8 h / 20 °C

With pyridine; sodium azide; boron trifluoride diethyl etherate; thiamine diphosphate; acetic acid; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 7: aza-Wittig-type reaction;
DOI:10.1002/ejoc.200300731

Reference yield:

: 79241-32-0
1-O-acetyl-2,3-O-isopropylidene-α-D-mannofuranose

: 714967-39-2
1,6-di-O-acetyl-5-deoxy-2,3-O-isopropylidene-5-(N'-phenylureido)-β-L-gulofuranose

Guidance literature:: Multi-step reaction with 7 steps

1: 84 percent / pyridine / 36 h / 20 °C

2: CH₂Cl₂ / 1 h / -25 °C

3: 1.8 g / NaN₃ / dimethylformamide / 18 h / 20 °C

4: 80 percent / BF₃*Et₂O / methanol; CH₂Cl₂ / 2 h / 0 - 20 °C

5: 85 percent / pyridine

6: 56 percent / TPP / toluene / 18 h / 20 °C

7: 81 percent / TFA / acetone; H₂O / 8 h / 20 °C

With pyridine; sodium azide; boron trifluoride diethyl etherate; thiamine diphosphate; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 6: aza-Wittig-type reaction;
DOI:10.1002/ejoc.200300731