(1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane>

Base Information

Chemical Name:(1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane>
CAS No.:148291-33-2
Molecular Formula:C₂₀H₂₇N₃O₅
Molecular Weight:389.451
Hs Code.:

Synonyms:(1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane>

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Chemical Property of (1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane>

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Technology Process of (1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane>

There total 7 articles about (1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane> 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:

: 97747-51-8
(1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol

: 148291-33-2
(1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane>

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / AgF, pyridine / 20 h / Ambient temperature

2: 91 percent / MCPBA, aq. phosphate buffer pH 8 / 1,2-dichloro-ethane / 50 h / Ambient temperature

3: 1) conc. H₂SO₄, 2) pyridine / 1) acetone, reflux, 3 h, 2) r.t., overnight

4: 54 percent / NaN₃ / dimethylformamide / 95 h / 90 °C

5: 1M methanolic NaOMe / 1 h / Ambient temperature

6: p-TsOH*H₂O / dimethylformamide / 1 h / Ambient temperature

7: 1) NaH / 1) DMF, 0.5 h, 2) 0.5 h

With pyridine; sodium azide; phosphate buffer pH 8; sulfuric acid; sodium methylate; silver fluoride; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

Reference yield:

: 148347-70-0
(1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane

: 148291-33-2
(1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane>

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / MCPBA, aq. phosphate buffer pH 8 / 1,2-dichloro-ethane / 50 h / Ambient temperature

2: 1) conc. H₂SO₄, 2) pyridine / 1) acetone, reflux, 3 h, 2) r.t., overnight

3: 54 percent / NaN₃ / dimethylformamide / 95 h / 90 °C

4: 1M methanolic NaOMe / 1 h / Ambient temperature

5: p-TsOH*H₂O / dimethylformamide / 1 h / Ambient temperature

6: 1) NaH / 1) DMF, 0.5 h, 2) 0.5 h

With pyridine; sodium azide; phosphate buffer pH 8; sulfuric acid; sodium methylate; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

Reference yield:

: (3S,4S,5S,6R,7R)-4,5,6-triacetoxy-7-bromo-1-oxaspiro<2.5>octane

: 148291-33-2
(1R,2S,4S,5S,6R)-4-azido-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolane>

Guidance literature:: Multi-step reaction with 5 steps

1: 1) conc. H₂SO₄, 2) pyridine / 1) acetone, reflux, 3 h, 2) r.t., overnight

2: 54 percent / NaN₃ / dimethylformamide / 95 h / 90 °C

3: 1M methanolic NaOMe / 1 h / Ambient temperature

4: p-TsOH*H₂O / dimethylformamide / 1 h / Ambient temperature

5: 1) NaH / 1) DMF, 0.5 h, 2) 0.5 h

With pyridine; sodium azide; sulfuric acid; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;