Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl ester

Base Information

Chemical Name:Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl ester
CAS No.:404353-56-6
Molecular Formula:C₃₃H₄₃NO₆
Molecular Weight:549.708
Hs Code.:

Synonyms:Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl ester

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Chemical Property of Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl ester

There total 17 articles about Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl 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: 80.0%

: Benzyl-[3-((2R,3R,4R)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-furan-2-yl)-propyl]-carbamic acid tert-butyl ester

: 404353-56-6
Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;
DOI:10.1016/S0957-4166(01)00400-1

Reference yield:

: 72277-36-2
3-O-benzyl-1,2-O-isopropylidene-5,6-dideoxy-α-D-xylo-heptofuranose

: 404353-56-6
Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: pyridine / CH₂Cl₂ / 6 h / 20 °C

2: 1.2 g / NaN₃ / dimethylformamide / 12 h / 90 °C

3: 2.0 g / LiAlH₄ / tetrahydrofuran / 12 h / 20 °C

4: 2.10 g / Et₃N / CH₂Cl₂ / 3 h / 20 °C

5: 80 percent / Na; liquid NH₃ / tetrahydrofuran / 2 h / -78 °C

6: 1.5 g / pyridinium dichromate / CH₂Cl₂ / 4 h / 0 °C

7: 1.14 g / NaBH₄ / methanol / 2 h / 20 °C

8: 74 percent / NaH / dimethylformamide / 0 °C

9: AcCl / 6 h / Heating

10: 0.38 g / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

11: 75 percent / NaH / dimethylformamide

12: aq. AcOH; aq. HCl / 4 h / 80 °C

13: 0.58 g / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

14: 80 percent / NaBH₄ / methanol / 1 h / 20 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; sodium azide; ammonia; sodium; sodium hydride; acetic acid; triethylamine; acetyl chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(01)00400-1

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 404353-56-6
Benzyl-((4R,5R,6S)-5,6-bis-benzyloxy-4,7-dihydroxy-heptyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 0.58 g / Et₃N / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 80 percent / NaBH₄ / methanol / 1 h / 20 °C

With sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;
DOI:10.1016/S0957-4166(01)00400-1