(5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one

Base Information

• Chemical Name: (5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one
• CAS No.: 872345-44-3
• Molecular Formula: C₁₆H₁₉N₃O₅
• Molecular Weight: 333.344

Synonyms:(5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one

Chemical Property of (5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one

Chemical Property:

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Technology Process of (5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one

There total 4 articles about (5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one 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: 93.4%

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose (872345-43-2) → (5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one (872345-44-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2005.09.043

Reference yield:

3-O-benzoyl-4-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-L-sorbopyranose (872345-41-0) → (5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one (872345-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / LiN₃ / dimethylformamide / 6 h / 100 °C

2: 97 percent / NaOMe / methanol / 24 h / 20 °C

3: 93.4 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With lithium azide; sodium methylate; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide; 3: Dess-Martin oxidation;

DOI:10.1016/j.tet.2005.09.043

Reference yield:

5-azido-3-O-benzoyl-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose (872345-42-1) → (5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one (872345-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NaOMe / methanol / 24 h / 20 °C

2: 93.4 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With sodium methylate; Dess-Martin periodane; In methanol; dichloromethane; 2: Dess-Martin oxidation;

DOI:10.1016/j.tet.2005.09.043

upstream raw materials:

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose

3-O-benzoyl-4-O-benzyl-5-deoxy-5-iodo-1,2-O-isopropylidene-α-L-sorbopyranose

5-azido-3-O-benzoyl-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-fructopyranose

Downstream raw materials:

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

5-azido-3,4-di-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

(3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline

(2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrrolidine

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