(1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane

Base Information

Chemical Name:(1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane
CAS No.:931396-15-5
Molecular Formula:C₁₅H₂₅NO₅
Molecular Weight:299.367
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane

Chemical Property:

Purity/Quality:

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Technology Process of (1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane

There total 6 articles about (1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane 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:

: 521964-59-0
tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate

: 635318-02-4
(1α,3β,5α)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-oxabicyclo[3.1.0]hexane-3-carboxylic acid 1,1-dimethylethyl ester

: 931396-15-5,635318-02-4
(1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane

Guidance literature:: tert-butyl 1-tert-butoxycarbonylaminocyclopent-3-enecarboxylate; With sulfuric acid; In ethyl acetate; for 0.0833333h; Large scale;

With magnesium monoperoxyphthalate hydrate; tetra(n-butyl)ammonium hydrogensulfate; In water; ethyl acetate; at 22 ℃; for 22h; Overall yield = 8.70 kg; Large scale;
DOI:10.1021/op060225f

Reference yield:

: 42726-73-8
methyl t-butyl malonate

: 931396-15-5,635318-02-4
(1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane

Guidance literature:: Multi-step reaction with 6 steps

1.1: lithium hydride / tetrahydrofuran / 0.5 h / 40 - 45 °C / Inert atmosphere; Large scale

1.2: 5.3 h / 40 °C / Inert atmosphere; Large scale

1.3: 2 h / 25 - 30 °C / Inert atmosphere; Large scale

2.1: triethylamine; thionyl chloride / toluene; tert-butyl methyl ether / 1.75 h / 0 - 23 °C / Large scale

3.1: tetra(n-butyl)ammonium hydrogensulfate; sodium azide / toluene; tert-butyl methyl ether; water / 23 °C / Large scale

4.1: toluene / 1 h / 90 - 100 °C

5.1: toluene; tert-butyl alcohol / 1.67 h / 0 - 23 °C / Large scale

5.2: 20 - 30 °C / Large scale

6.1: sulfuric acid / ethyl acetate / 0.08 h / Large scale

6.2: 22 h / 22 °C / Large scale

With thionyl chloride; sodium azide; sulfuric acid; tetra(n-butyl)ammonium hydrogensulfate; lithium hydride; triethylamine; In tetrahydrofuran; tert-butyl methyl ether; water; ethyl acetate; toluene; tert-butyl alcohol; 4.1: |Curtius Rearrangement;
DOI:10.1021/op060225f

Reference yield:

: 635318-61-5
3-cyclopentene-1,1-dicarboxylic acid mono(1,1-dimethylethyl) ester

: 931396-15-5,635318-02-4
(1S,3S,5R)-3-(tert-butoxycarbonylamino)-3-(tert-butoxycarbonyl)-6-oxabicyclo[3.1.O]hexane

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine; thionyl chloride / toluene; tert-butyl methyl ether / 1.75 h / 0 - 23 °C / Large scale

2.1: tetra(n-butyl)ammonium hydrogensulfate; sodium azide / toluene; tert-butyl methyl ether; water / 23 °C / Large scale

3.1: toluene / 1 h / 90 - 100 °C

4.1: toluene; tert-butyl alcohol / 1.67 h / 0 - 23 °C / Large scale

4.2: 20 - 30 °C / Large scale

5.1: sulfuric acid / ethyl acetate / 0.08 h / Large scale

5.2: 22 h / 22 °C / Large scale

With thionyl chloride; sodium azide; sulfuric acid; tetra(n-butyl)ammonium hydrogensulfate; triethylamine; In tert-butyl methyl ether; water; ethyl acetate; toluene; tert-butyl alcohol; 3.1: |Curtius Rearrangement;
DOI:10.1021/op060225f