(3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane

Base Information

Chemical Name:(3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane
CAS No.:94062-88-1
Molecular Formula:C₁₅H₂₁NO₃
Molecular Weight:263.337
Hs Code.:

Synonyms:(3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane

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Chemical Property of (3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane

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Technology Process of (3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane

There total 9 articles about (3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]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: 61.7%

: 93978-88-2
Methanesulfonic acid (2S,3R,4R,6S)-3-benzyloxy-4-cyano-6-methoxy-2-methyl-tetrahydro-pyran-4-yl ester

: 94062-88-1
(3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; for 2h; Heating;
DOI:10.1246/bcsj.57.2538

Reference yield:

: 83497-33-0
methyl 4-O-benzoyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside

: 94062-88-1
(3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane

Guidance literature:: Multi-step reaction with 7 steps

1: 92.2 percent / Ag₂O / dimethylformamide / 24 h

2: 1) AgF, 2) H₂ / 2) 10percent Pd/C / 1) pyridine, 40 h, 2) CH₃OH-CH₃CO₂H, overnight

3: 62.2 percent / CF₃CO₂H / CH₂Cl₂; cyclohexane / 72 h / Ambient temperature

4: 88.7 percent / CH₃ONa / methanol / Ambient temperature; overnight

5: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / Heating; molecular sieves 3A, overnight

6: pyridine

7: 61.7 percent / LiAlH₄ / diethyl ether / 2 h / Heating

With pyridine; lithium aluminium tetrahydride; hydrogen; sodium methylate; silver fluoride; pyridinium chlorochromate; trifluoroacetic acid; silver(l) oxide; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1246/bcsj.57.2538

Reference yield:

: 93960-55-5
methyl 3-O-benzoyl-4-O-benzyl-6-bromo-2,6-dideoxy-α-D-ribo-hexopyranoside

: 94062-88-1
(3S,4S,5S,7S)-4-Benzyloxy-7-methoxy-5-methyl-6-oxa-1-aza-spiro[2.5]octane

Guidance literature:: Multi-step reaction with 6 steps

1: 1) AgF, 2) H₂ / 2) 10percent Pd/C / 1) pyridine, 40 h, 2) CH₃OH-CH₃CO₂H, overnight

2: 62.2 percent / CF₃CO₂H / CH₂Cl₂; cyclohexane / 72 h / Ambient temperature

3: 88.7 percent / CH₃ONa / methanol / Ambient temperature; overnight

4: 84 percent / pyridinium chlorochromate / CH₂Cl₂ / Heating; molecular sieves 3A, overnight

5: pyridine

6: 61.7 percent / LiAlH₄ / diethyl ether / 2 h / Heating

With pyridine; lithium aluminium tetrahydride; hydrogen; sodium methylate; silver fluoride; pyridinium chlorochromate; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; cyclohexane;
DOI:10.1246/bcsj.57.2538