(+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.0^2,6>decane

Base Information

• Chemical Name: (+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.0^2,6>decane
• CAS No.: 101244-87-5
• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.44

Synonyms:

Chemical Property of (+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.0^2,6>decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.0^2,6>decane

There total 21 articles about (+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.0^2,6>decane 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: 53.0%

C20H26O5 → (+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.02,6>decane (101244-87-5)

Guidance literature:

With potassium hydroxide; hydrazine hydrate; In diethylene glycol; 140 deg C, 70 min; 140 -> 200 deg C, 30 min; 200 deg C, 1 h;

DOI:10.1016/S0040-4020(01)81204-7

Reference yield:

methyl cyclopent-2-ene-1-carboxylate (2258-56-2) → (+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.02,6>decane (101244-87-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 92 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 15 h / Ambient temperature

2: 92 percent / NaOMe / methanol / 2.5 h / Ambient temperature

3: 10.9 g / imidazole / dimethylformamide / 2 h / Ambient temperature

4: 1N NaOH / methanol / 12 h / Ambient temperature

5: 96 percent / dicyclohexylcarbidiimide, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

6: 25 percent / acetonitrile / 15 °C / Irradiation

7: 1.) DIBAH, 2.) p-toluenesulfonic acid / 1.) THF, hexane, -78 deg C, 1 h, 2.) CH₂Cl₂, room temp., 30 min

8: 91 percent / 40percent aq. HF / methanol / 3 h / Ambient temperature

9: 1.) diethyl azodicarboxylate, benzoic acid, PPh₃, 2.) 15percent aq. NaOH / 1.) THF, room temp., 30 min, 2.) MeOH, room temp., 17 h

10: 87 percent / 50percent NaH / dimethylformamide / 1.5 h / Ambient temperature

11: 1.) AcOH, 2.) CrO₃, H₂SO₄ / 1.) THF, water, reflux, 18 h, 2.) acetone, water, room temp., 1 h

12: 2.) pyridinium p-toluenesulfonate / 1.) THF, ether, -78 deg C, 25 min, 2.) CH₂Cl₂, room temp., 16 h

13: DIBAH / toluene; hexane / 1 h / -78 °C

14: 53 percent / 80percent H₂NNH₂*H₂O, KOH / bis-(2-hydroxy-ethyl) ether / 140 deg C, 70 min; 140 -> 200 deg C, 30 min; 200 deg C, 1 h

With 1H-imidazole; chromium(VI) oxide; dmap; potassium hydroxide; sodium hydroxide; sulfuric acid; hydrogen fluoride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; triphenylphosphine; benzoic acid; diethylazodicarboxylate; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; diethylene glycol;

DOI:10.1016/S0040-4020(01)81204-7

Reference yield:

methyl 2,3-epoxycyclopentane-1-carboxylate (162086-60-4,170423-00-4,170423-01-5) → (+)-(1S,2S,6S,7S,8S)-8-benzyloxy-3-hydroxymethyl-5-methoxy-1,5-dimethyl-4-oxatricyclo<5.3.0.02,6>decane (101244-87-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 92 percent / NaOMe / methanol / 2.5 h / Ambient temperature

2: 10.9 g / imidazole / dimethylformamide / 2 h / Ambient temperature

3: 1N NaOH / methanol / 12 h / Ambient temperature

4: 96 percent / dicyclohexylcarbidiimide, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

5: 25 percent / acetonitrile / 15 °C / Irradiation

6: 1.) DIBAH, 2.) p-toluenesulfonic acid / 1.) THF, hexane, -78 deg C, 1 h, 2.) CH₂Cl₂, room temp., 30 min

7: 91 percent / 40percent aq. HF / methanol / 3 h / Ambient temperature

8: 1.) diethyl azodicarboxylate, benzoic acid, PPh₃, 2.) 15percent aq. NaOH / 1.) THF, room temp., 30 min, 2.) MeOH, room temp., 17 h

9: 87 percent / 50percent NaH / dimethylformamide / 1.5 h / Ambient temperature

10: 1.) AcOH, 2.) CrO₃, H₂SO₄ / 1.) THF, water, reflux, 18 h, 2.) acetone, water, room temp., 1 h

11: 2.) pyridinium p-toluenesulfonate / 1.) THF, ether, -78 deg C, 25 min, 2.) CH₂Cl₂, room temp., 16 h

12: DIBAH / toluene; hexane / 1 h / -78 °C

13: 53 percent / 80percent H₂NNH₂*H₂O, KOH / bis-(2-hydroxy-ethyl) ether / 140 deg C, 70 min; 140 -> 200 deg C, 30 min; 200 deg C, 1 h

With 1H-imidazole; chromium(VI) oxide; dmap; potassium hydroxide; sodium hydroxide; sulfuric acid; hydrogen fluoride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; dicyclohexyl-carbodiimide; triphenylphosphine; benzoic acid; diethylazodicarboxylate; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; diethylene glycol;

DOI:10.1016/S0040-4020(01)81204-7

upstream raw materials:

(-)-(1S,5R,8S,9S,10S,13S)-8-benzyloxy-11-methoxy-11-methyl-3,12-dioxatetracyclo<8.2.1.0.^5,90^5,13>tridecan-4-one

methyl cyclopent-2-ene-1-carboxylate

benzyl bromide

3-hydroxy-cyclopentene-1-carboxylic acid methyl ester

Downstream raw materials:

(-)-(1S,2S,6S,7S,8S)-8-benzyloxy-1,5-dimethyltricyclo<5.3.0.0^2,6>dec-4-en-3-one

(+)-(1S,4S,5S)-6,7-diacetyl-4-benzyloxy-1-methylbicyclo<3.2.0>heptane

(-)-(1R,2S,3S,5R,6R,7S,10R)-5-methoxymethoxy-6,10-dimethyltricyclo<5.3.0.0^2,6>decan-3-yl p-toluenesulfonate

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