(1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,6-dioxabicyclo[3.3.0]octane

Base Information

Chemical Name:(1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,6-dioxabicyclo[3.3.0]octane
CAS No.:849624-17-5
Molecular Formula:C₂₁H₃₃NO₅Si
Molecular Weight:407.582
Hs Code.:

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

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

There total 11 articles about (1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-(tert-butyldimethylsilyloxy)-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: 99.0%

: N-((3S,3aR,6R,6aS)-6-Benzyloxy-2-hydroxy-hexahydro-furo[3,2-b]furan-3-yl)-acetamide

: 18162-48-6
tert-butyldimethylsilyl chloride

: 849624-17-5
(1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,6-dioxabicyclo[3.3.0]octane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 3h;
DOI:10.1016/j.tet.2008.10.014

Reference yield:

: 14362-29-9
α-D-glucurono-γ-lactone

: 849624-17-5
(1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,6-dioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 11 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

8.1: PPh₃; H₂O / tetrahydrofuran; CH₂Cl₂

9.1: pyridine / CH₂Cl₂

10.1: aq. AcOH / 90 °C

11.1: imidazole / dimethylformamide

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; sodium azide; sulfuric acid; water; di(n-butyl)tin oxide; acetic acid; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; silver(l) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-837198

Reference yield:

: 5111-13-7
(1S,3R,4R,5S,8S)-8-benzyloxy-7-keto-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane

: 849624-17-5
(1S,4S,5R,8R)-4-acetamido-8-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,6-dioxabicyclo[3.3.0]octane

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / LiAlH₄ / tetrahydrofuran

2.1: TsCl; Bu₂SnO; Et₃N / CH₂Cl₂

2.2: 73 percent / NaH / tetrahydrofuran

3.1: 99 percent / aq. HCl

4.1: pyridine / CH₂Cl₂

5.1: NaN₃ / dimethylformamide / 60 °C

6.1: PPh₃; H₂O / tetrahydrofuran; CH₂Cl₂

7.1: pyridine / CH₂Cl₂

8.1: aq. AcOH / 90 °C

9.1: imidazole / dimethylformamide

With pyridine; 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; sodium azide; water; di(n-butyl)tin oxide; acetic acid; triethylamine; p-toluenesulfonyl chloride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2004-837198