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

Base Information

• Chemical Name: (1S,3S,4R,5S,6S)-4,5-bis(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptane
• CAS No.: 702659-55-0
• Molecular Formula: C₂₉H₃₀Cl₂O₅
• Molecular Weight: 529.46

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

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

Chemical Property:

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

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

methyl 2,3,6-tri-O-benzyl-4-O-(1H-imidazol-1-ylsulfonyl)-α-D-galactopyranoside (432038-84-1) → (1S,3S,4R,5S,6S)-4,5-bis(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptane (702659-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / potassium tert-butoxide / dimethylformamide / 20 °C

2: 47 percent / benzyltriethylammonium chloride; sodium hydroxide / H₂O / 2 h / 20 °C

With sodium hydroxide; potassium tert-butylate; N-benzyl-N,N,N-triethylammonium chloride; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.03.018

Reference yield: 68.0%

(1S,3S,4R,5S,6S)-4,5-bis(benzyloxy)-1-[(benzyloxy)methyl]-7,7-dichloro-3-methoxy-2-oxabicyclo[4.1.0]heptane (702659-55-0) → (1S,3S,4R,5S,6S)-4,5-bis(benzyloxy)-1-[(benzyloxy)methyl]-3-methoxy-2-oxabicyclo[4.1.0]heptane

Guidance literature:

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

DOI:10.1016/j.tet.2004.03.018

upstream raw materials:

methyl 2,3,6-tri-O-benzyl-4-O-(1H-imidazol-1-ylsulfonyl)-α-D-galactopyranoside

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