(1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane

Base Information

Chemical Name:(1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane
CAS No.:849624-15-3
Molecular Formula:C₁₄H₁₇N₃O₄
Molecular Weight:291.307
Hs Code.:

Synonyms:(1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane

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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,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane

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Technology Process of (1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane

There total 7 articles about (1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane 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: 87.0%

: methyl 3,6-anhydro-5-O-benzyl-2-O-trifluoromethanesulfonyl-D-glucofuranoside

: 849624-15-3
(1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 3h;
DOI:10.1016/j.tetasy.2004.09.012

Reference yield:

: 849624-14-2
(1R,4R,5R,8R)-8-benzyloxy-3-methoxy-4-hydroxy-2,6-dioxabicyclo[3.3.0]octane

: 849624-15-3
(1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / CH₂Cl₂

2: NaN₃ / dimethylformamide / 60 °C

With pyridine; sodium azide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-837198

Reference yield:

: 14362-29-9
α-D-glucurono-γ-lactone

: 849624-15-3
(1S,4S,5R,8R)-4-azido-8-benzyloxy-3-methoxy-2,6-dioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 7 steps

1.1: H₂SO₄

2.1: Ag₂O / ethyl acetate

3.1: 93 percent / LiAlH₄ / tetrahydrofuran

4.1: TsCl; Bu₂SnO; Et₃N / CH₂Cl₂

4.2: 73 percent / NaH / tetrahydrofuran

5.1: 99 percent / aq. HCl

6.1: pyridine / CH₂Cl₂

7.1: NaN₃ / dimethylformamide / 60 °C

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; sodium azide; sulfuric acid; di(n-butyl)tin oxide; triethylamine; p-toluenesulfonyl chloride; silver(l) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-837198