(1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene

Base Information

• Chemical Name: (1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene
• CAS No.: 709654-96-6
• Molecular Formula: C₂₇H₃₀O₅
• Molecular Weight: 434.532

Synonyms:(1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene

Chemical Property of (1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene

Chemical Property:

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Technology Process of (1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene

There total 4 articles about (1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene 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: 50.0%

(1R,3R,4R,5S,6R)-4,5-bis-benzyloxy-3-hydroxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene (709654-95-5) + allyl alcohol (107-18-6) → (1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene (709654-96-6)

Guidance literature:

With 4 A molecular sieve; Montmorillonite K-10 clay; In dichloromethane; at 20 ℃;

DOI:10.1039/b401699h

Reference yield:

(2S,3R,4S,4aR,8aR)-3,4-Bis-benzyloxy-2,3,4,4a,6,8a-hexahydro-pyrano[3,2-b]pyran-2-ol → (1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene (709654-96-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 300 mg / acetic anhydride; DMSO / 17 h / 20 °C

2: 21 percent / diethyl ether / -78 °C

3: 50 percent / Montmorillonite K-10 clay; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; Montmorillonite K-10 clay; acetic anhydride; dimethyl sulfoxide; In diethyl ether; dichloromethane;

DOI:10.1039/b401699h

Reference yield:

(3R,4S,4aR,8aR)-3,4-Bis-benzyloxy-4,4a,6,8a-tetrahydro-3H-pyrano[3,2-b]pyran-2-one (709654-94-4) → (1R,3R,4R,5S,6R)-3-allyloxy-4,5-bis-benzyloxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene (709654-96-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 21 percent / diethyl ether / -78 °C

2: 50 percent / Montmorillonite K-10 clay; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

With 4 A molecular sieve; Montmorillonite K-10 clay; In diethyl ether; dichloromethane;

DOI:10.1039/b401699h

upstream raw materials:

(1R,3R,4R,5S,6R)-4,5-bis-benzyloxy-3-hydroxy-3-vinyl-2,7-dioxa-bicyclo[4.4.0]dec-9-ene

allyl alcohol

(3R,4S,4aR,8aR)-3,4-Bis-benzyloxy-4,4a,6,8a-tetrahydro-3H-pyrano[3,2-b]pyran-2-one

(1R,6R,8S,9R,10S)-9,10-bis(benzyloxy)-8-methoxy-2,7-dioxabicyclo[4.4.0]dec-4-ene

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