N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Base Information

Chemical Name:N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
CAS No.:155238-43-0
Molecular Formula:C₅₅H₅₈N₂O₁₀
Molecular Weight:907.073
Hs Code.:

N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

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Chemical Property of N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

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Technology Process of N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

There total 5 articles about N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 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:

: 93173-27-4
2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranosyl isothiocyanate

: 155238-43-0
N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: NEt₃ / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) r.t., 13 h

2: 1.) 2-chloro-1-methylpyridinium iodide, 2.) NEt₃ / 1.) CH₃CN, 0 deg C, 1 h, 2.) CH₃CN, 0 deg C, 1 h

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; In tetrahydrofuran;
DOI:10.7164/antibiotics.47.243

Reference yield:

: 144811-34-7
(1R,2R,3S,4R,5S)-2-Amino-5-benzyloxy-1-benzyloxymethyl-3,4-bis-methoxymethoxy-cyclopentanol

: 155238-43-0
N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 10percent HCl / methanol / 1.) 0 deg C, 5 min, 2.) 60 deg C, 4 h

2: NEt₃ / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) r.t., 13 h

3: 1.) 2-chloro-1-methylpyridinium iodide, 2.) NEt₃ / 1.) CH₃CN, 0 deg C, 1 h, 2.) CH₃CN, 0 deg C, 1 h

With hydrogenchloride; 2-chloro-1-methyl-pyridinium iodide; triethylamine; In tetrahydrofuran; methanol;
DOI:10.7164/antibiotics.47.243

Reference yield:

: 144811-29-0
<1R-(1α,2β,3α,4β,5β)>-5-Azido-2-(benzyloxy)-1-<(benzyloxy)methyl>-3,4-bis(methoxymethoxy)-1-cyclopentanol

: 155238-43-0
N-<<3aR-(3aα,4α,5β,6α,6aα)>-5-benzyloxy-4-benzyloxymethyl-3a,5,6,6a-tetrahydro-4H-cyclopentoxazole-4,6-diol-2-yl>amino-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / LiAlH₄ / diethyl ether / 4 h / 0 °C

2: 10percent HCl / methanol / 1.) 0 deg C, 5 min, 2.) 60 deg C, 4 h

3: NEt₃ / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) r.t., 13 h

4: 1.) 2-chloro-1-methylpyridinium iodide, 2.) NEt₃ / 1.) CH₃CN, 0 deg C, 1 h, 2.) CH₃CN, 0 deg C, 1 h

With hydrogenchloride; lithium aluminium tetrahydride; 2-chloro-1-methyl-pyridinium iodide; triethylamine; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.7164/antibiotics.47.243