isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate

Base Information

• Chemical Name: isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate
• CAS No.: 786702-77-0
• Molecular Formula: C₁₆H₃₁N₃O₆Si
• Molecular Weight: 389.524

Synonyms:isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate

Chemical Property of isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate

There total 2 articles about isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate 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: 43.0%

isopropyl (1R,2S,3S,4S,5R)-1-(tert-butyldimethylsilyloxy)-2,3-epoxy-4,5-dihydroxycyclohexane-1-carboxylate (786702-76-9) → isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate (786702-77-0)

Guidance literature:

With trimethylsilylazide; boron trifluoride diethyl etherate; In dichloromethane; for 2.6h; Heating;

DOI:10.1002/ejoc.200400282

Reference yield:

(1R,2S,3S,4S,5R)-1-(tert-butyldimethylsilyloxy)-2,3-epoxy-4-hydroxycyclohexane-1,5-carbolactone (504397-78-8) → isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate (786702-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / 2-propanol / benzene / 5 h / 75 °C

2: 43 percent / TMSN₃; BF₃*OEt₂ / CH₂Cl₂ / 2.6 h / Heating

With trimethylsilylazide; boron trifluoride diethyl etherate; isopropyl alcohol; In dichloromethane; benzene;

DOI:10.1002/ejoc.200400282

Reference yield: 94.0%

acetic anhydride (108-24-7) + isopropyl (1R,2S,3R,4R,5R)-3-azido-1-(tert-butyldimethylsilyloxy)-2,4,5-trihydroxycyclohexane-1-carboxylate (786702-77-0) → isopropyl (1R,2S,3R,4R,5R)-2,4,5-triacetoxy-3-azido-1-(tert-butyldimethylsilyloxy)cyclohexane-1-carboxylate

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200400282

upstream raw materials:

isopropyl (1R,2S,3S,4S,5R)-1-(tert-butyldimethylsilyloxy)-2,3-epoxy-4,5-dihydroxycyclohexane-1-carboxylate

(1R,2S,3S,4S,5R)-1-(tert-butyldimethylsilyloxy)-2,3-epoxy-4-hydroxycyclohexane-1,5-carbolactone

Downstream raw materials:

(1S,2S,3R,4R,5R)-3-azido-1-hydroxymethyl-1,2,4,5-cyclohexane-tetrol

(1R,2S,3R,4R,5R)-3-azido-1,2,4,5-tetrahydroxycyclohexane-1-carboxylic acid

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