(1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol

Base Information

• Chemical Name: (1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol
• CAS No.: 702659-49-2
• Molecular Formula: C₂₂H₂₄Cl₂O₅
• Molecular Weight: 439.336

Synonyms:(1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol

Chemical Property of (1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol

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Technology Process of (1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol

There total 1 articles about (1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-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: 61.0%

chloroform (67-66-3,8013-54-5) + methyl 2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside (134039-06-8) → (1S,3R,4R,5S,6S)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol + (1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol (702659-49-2)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In water; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2004.03.018

Reference yield: 90.0%

(1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol (702659-49-2) → (1R,3R,4R,5S,6R,7R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7-chloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tet.2004.03.018

Reference yield: 75.0%

(1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol (702659-49-2) → (1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[4.1.0]heptan-5-ol

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tet.2004.03.018

upstream raw materials:

chloroform

methyl 2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside

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