(1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane

Base Information

• Chemical Name: (1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane
• CAS No.: 228394-07-8
• Molecular Formula: C₂₈H₃₉N₃O₃Si
• Molecular Weight: 493.721

Synonyms:(1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane

Chemical Property of (1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane

There total 12 articles about (1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>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: 96.0%

t-butyldimethylsiyl triflate (69739-34-0) + (1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane (228394-01-2) → (1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane (228394-07-8)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo990010m

Reference yield:

(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol (156126-13-5) → (1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane (228394-07-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 57 percent / p-TsOH*H₂O / 2 h / Heating

2: 100 percent / TPAP, NMO, 4A MS / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

5: 88 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Heating

6: 100 percent / aq. HCl / tetrahydrofuran; methanol / 10 h / Heating

7: 80 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

8: 81 percent / NaN₃ / dimethylformamide / 10 h / 100 °C

9: 96 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; hydrogenchloride; sodium perborate; n-butyllithium; thionyl chloride; sodium azide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo990010m

Reference yield:

(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane (199122-41-3) → (1S,2S,3R,4R,5S)-4-azido-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane (228394-07-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Heating

2: 100 percent / aq. HCl / tetrahydrofuran; methanol / 10 h / Heating

3: 80 percent / SOCl₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

4: 81 percent / NaN₃ / dimethylformamide / 10 h / 100 °C

5: 96 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; hydrogenchloride; thionyl chloride; sodium azide; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo990010m

upstream raw materials:

t-butyldimethylsiyl triflate

(1S,2S,3R,4R,5S)-4-azido-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol

(1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

Downstream raw materials:

1-[(1S,2R,3R,4S,5S)-4,5-Bis-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-bicyclo[3.1.0]hex-2-yl]-3-((Z)-3-ethoxy-acryloyl)-isourea

dithiocarbonic acid O-[4-(3-benzoyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-1,2-bis-benzyloxymethyl-bicyclo[3.1.0]hex-3-yl] ester S-methyl ester

(1S,2S,4S,5S)-1,2-di<(benzyloxy)methyl>-4-<2,4-(1H,3H)-dioxopyrimidin-1-yl>bicyclo<3.1.0>hexane

(1S,2S,3R,4S,5S)-4-3-benzoyl-2,4-(1H)-dioxopyrimidin-1-yl>-3-(tert-butyldimethylsilyloxy)-1,2-di<(benzyloxy)methyl>bicyclo<3.1.0>hexane

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