(+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

Base Information

• Chemical Name: (+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane
• CAS No.: 207276-55-9
• Molecular Formula: C₁₄H₂₄O₅
• Molecular Weight: 272.342

Synonyms:(+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

Chemical Property of (+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

Chemical Property:

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Technology Process of (+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

There total 1 articles about (+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]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: 77.0%

(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane (289667-12-5) + allyl-trimethyl-silane (762-72-1) → (+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (207276-55-9) + (+)-(1R,5R,6R,8R,10S)-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (289667-00-1)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 0.166667h;

DOI:10.1021/ol052943c

Reference yield:

(+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (207276-55-9) → (1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (218965-70-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Jones reagent / acetone / 0.5 h

2.1: 6.3 mg / Et₃N; (PhO)2PON₃; 4 Angstroem molecular sieves / tetrahydrofuran / 5.5 h / 65 °C

3.1: 78 percent / DMAP; LHMDS / tetrahydrofuran; CH₂Cl₂ / -78 - 0 °C

4.1: 93 percent / TBAF / tetrahydrofuran; CH₂Cl₂ / 0.08 h / 0 °C

5.1: BuLi; TMEDA / tetrahydrofuran / 0.5 h / -78 °C

5.2: tetrahydrofuran / 2.5 h / -78 °C

With dmap; n-butyllithium; jones reagent; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetone; 1.1: Jones oxidation / 2.1: Curtius rearrangement;

DOI:10.1021/jo060803q

Reference yield:

(+)-(1R,5R,6R,8R,10S)-5-(hydroxy)methyl-10-methoxy-9,9-dimethyl-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (207276-55-9) → (1S,5R,6S,8R,10S)-10-methoxy-9,9-dimethyl-5-{[(2R,3R,4RS)-2,3-dimethyl-4-phenylselenylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane (880766-74-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Jones reagent / acetone / 0.5 h

2.1: 6.3 mg / molecular sieves 4 Angstroem; Et₃N; diphenylphosphoryl azide / tetrahydrofuran / 5.5 h / 65 °C

3.1: 78 percent / LiHMDS; DMAP / tetrahydrofuran; CH₂Cl₂ / -78 - 0 °C

4.1: 93 percent / TBAF / tetrahydrofuran / 0.08 h / 0 °C

5.1: BuLi / tetrahydrofuran / 0.25 h / -78 °C

5.2: 50 percent / TMEDA / tetrahydrofuran / 2.5 h / -78 °C

With dmap; n-butyllithium; jones reagent; 4 A molecular sieve; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetone; 1.1: Jones oxidation / 2.1: Cutius rearrangement;

DOI:10.1021/ol052943c

upstream raw materials:

(1R,5R,6R,8RS,10S)-8-acetoxy-5-(tert-butyldiphenylsilyloxy)methyl-9,9-dimethyl-10-methoxy-2,4,7-trioxabicyclo[4.4.0]decane

allyl-trimethyl-silane

Downstream raw materials:

(1S,5S,6S,8S,10R)-5-{[(2R,3R,4R)-2,3-Dimethyl-4-phenylselanylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-9,9-dimethyl-10-methoxy-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

(1S,5R,6S,8R,10S)-10-methoxy-9,9-dimethyl-5-{[(2R,3R,4RS)-2,3-dimethyl-4-phenylselenylmethyl-3,4-dihydro-2H-pyran-6-yl]oxoethanamido}-8-(prop-2-enyl)-2,4,7-trioxabicyclo[4.4.0]decane

Benzoic acid (S)-((4S,4aS,6R,8S,8aR)-6-allyl-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid (S)-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-(2-oxo-ethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-methyl ester

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