(1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane

Base Information

• Chemical Name: (1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane
• CAS No.: 148347-70-0
• Molecular Formula: C₁₃H₁₇BrO₆
• Molecular Weight: 349.178
• Mol file: 148347-70-0.mol

Synonyms:

Chemical Property of (1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane

There total 1 articles about (1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane 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: 92.0%

(1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol (97747-51-8) → (1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane (148347-70-0)

Guidance literature:

With pyridine; silver fluoride; for 20h; Ambient temperature;

Reference yield:

(1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane (148347-70-0) → C14H27NO10

Guidance literature:

Multi-step reaction with 12 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

7: 80 percent / Ph₃P / CH₂Cl₂; H₂O / 48 h / Ambient temperature

8: 78 percent / propan-2-ol / 25 h / 120 °C

10: 89 percent / Bu₃SnH, AIBN / toluene / 2 h / Heating

11: 3M HCl / 2 h / 60 °C

12: H₂ / Pd/C / ethanol / 760 Torr / Ambient temperature

With pyridine; hydrogenchloride; sodium azide; 2,2'-azobis(isobutyronitrile); phosphate buffer pH 8; sulfuric acid; hydrogen; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

Reference yield:

(1R)-(1,3/2,4)-2,3,4-triacetoxy-1-bromo-5-methylenecyclohexane (148347-70-0) → 4,5,6-triacetoxy-1-(acetoxymethyl)cyclohex-2-enol

Guidance literature:

Multi-step reaction with 3 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: 6.6 percent / NaN₃ / dimethylformamide / 95 h / 90 °C

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

upstream raw materials:

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

Downstream raw materials:

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

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

(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>

(1S,2R,3S,4S,6S)-4-(acetoxymethyl)-6-azido-4-hydroxycyclohexane-1,2,3-triyl triacetate

Refernces