(4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol

Base Information

• Chemical Name: (4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol
• CAS No.: 160695-20-5
• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.488

Synonyms:(4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol

Chemical Property of (4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol

Chemical Property:

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Technology Process of (4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol

There total 8 articles about (4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol 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: 60.0%

(3aS,6aS)-3-<(E)-allylidene>-6a-(methoxyphenoxymethyl)-5',5'-dimethyl-2,3,3a,6a-tetrahydrospiro<4H-cyclopentafuran-4,2'-<1,3>dioxan>-2-ol → (4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol (160695-20-5)

Guidance literature:

With sodium tetrahydroborate; potassium tert-butylate; In isopropyl alcohol; for 12h; Ambient temperature;

Reference yield:

(8,8-Dimethyl-2-oxo-6,10-dioxa-spiro[4.5]dec-3-en-1-yl)-acetic acid ethyl ester → (4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol (160695-20-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 45 percent / CH₂Cl₂ / 168 h / Ambient temperature

2: 1.) K₂CO₃, Bu₃SnCH₂I, 18-crown-6, 2.) BuLi

3: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 30 min

4: Et₃N / CH₂Cl₂ / 0.25 h

5: DBU / CH₂Cl₂ / 72 h

6: 96 percent / DIBAL / diethyl ether / 0.25 h / -78 °C

7: 60 percent / NaBH₄, t-BuOK / propan-2-ol / 12 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; 18-crown-6 ether; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; tri-n-butylstannylmethyl iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In diethyl ether; dichloromethane; isopropyl alcohol;

Reference yield:

(5S)-5-ethoxycarbonylmethyl-5',5'-dimethylspirodioxan>-4-one (148727-46-2) → (4S,5S)-5-<1-(hydroxymethyl)-(E)-buta-1,3-dienyl>-4-(4-methoxyphenoxymethyl)-5',5'-dimethylspirodioxan>-4-ol (160695-20-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) K₂CO₃, Bu₃SnCH₂I, 18-crown-6, 2.) BuLi

2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 30 min

3: Et₃N / CH₂Cl₂ / 0.25 h

4: DBU / CH₂Cl₂ / 72 h

5: 96 percent / DIBAL / diethyl ether / 0.25 h / -78 °C

6: 60 percent / NaBH₄, t-BuOK / propan-2-ol / 12 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; 18-crown-6 ether; potassium tert-butylate; diisobutylaluminium hydride; potassium carbonate; tri-n-butylstannylmethyl iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; In diethyl ether; dichloromethane; isopropyl alcohol;

upstream raw materials:

(5S)-5-ethoxycarbonylmethyl-5',5'-dimethylspirodioxan>-4-one

(3aS,6aS)-6a-(4-methoxyphenoxymethyl)-5',5'-dimethyl-3a,6a-dihydrospiro<4H-cyclopentafuran-4,2'-<1,3>dioxan>-2(3H)-one

(3R,3aS,6aS)-6a-(4-methoxyphenoxymethyl)-5',5'-dimethyl-3-<(1R)-1-hydroxyallyl>-3a,6a-dihydrospiro<4H-cyclopentafuran-4,2'-<1,3>dioxan>-2(3H)-one

C₂₄H₃₀O₉S

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