1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Base Information

• Chemical Name: 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose
• CAS No.: 144811-37-0
• Molecular Formula: C₅₅H₅₈N₂O₁₀
• Molecular Weight: 907.073
• Mol file: 144811-37-0.mol

Synonyms:1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Chemical Property of 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

There total 6 articles about 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 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:

(1R,2R,3S,4R,5S)-2-Amino-5-benzyloxy-1-benzyloxymethyl-3,4-bis-methoxymethoxy-cyclopentanol (144811-34-7) → 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (144811-37-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 10percent HCl / methanol / 1.) 0 deg C, 5 min, 2. ) 50 deg C, 5 h

2: Et₃N / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) r.t., 18 h

3: 2-chloro-3-ethylbenzoxazolium tetrafluoroborate / acetonitrile / 1 h / 0 °C

4: Et₃N / acetonitrile / 1 h / 0 °C

With hydrogenchloride; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; triethylamine; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/jo00083a023

Reference yield:

<1R-(1α,2β,3α,4β,5β)>-5-Azido-2-(benzyloxy)-1-<(benzyloxy)methyl>-3,4-bis(methoxymethoxy)-1-cyclopentanol (144811-29-0) → 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (144811-37-0)

Guidance literature:

Multi-step reaction with 5 steps

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

2: 10percent HCl / methanol / 1.) 0 deg C, 5 min, 2. ) 50 deg C, 5 h

3: Et₃N / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) r.t., 18 h

4: 2-chloro-3-ethylbenzoxazolium tetrafluoroborate / acetonitrile / 1 h / 0 °C

5: Et₃N / acetonitrile / 1 h / 0 °C

With hydrogenchloride; lithium aluminium tetrahydride; 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; acetonitrile;

DOI:10.1021/jo00083a023

Reference yield:

((1R,2R,3S,4R,5S)-3-Benzyloxy-2-benzyloxymethyl-2,4,5-trihydroxy-cyclopentyl)-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-carbodiimide → 1-<<<3aR-(3aα,4α,5β,6α,6aα)>-5-(Benzyloxy)-4-<(benzyloxy)methyl>-3a,5,6,6a-tetrahydro-4,6-dihydroxy-4H-cyclopentoxazol-2-yl>amino>-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (144811-37-0)

Guidance literature:

With triethylamine; In acetonitrile; at 0 ℃; for 1h; Yield given;

DOI:10.1021/jo00083a023

upstream raw materials:

N-(2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl)-N'-<<1R-(1α,2β,3α,4β,5β)>-2-(benzyloxy)-1-<(benzyloxy)methyl>-1,3,4-trihydroxycyclopent-5-yl>thiourea

2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl isothiocyanate

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

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

Downstream raw materials:

trehazolin