(1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride

Base Information

• Chemical Name: (1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride
• CAS No.: 144811-35-8
• Molecular Formula: C₂₀H₂₅NO₅*ClH
• Molecular Weight: 395.883
• Mol file: 144811-35-8.mol

Synonyms:(1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride

Chemical Property of (1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride

There total 2 articles about (1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride 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) → (1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride (144811-35-8)

Guidance literature:

With hydrogenchloride; In methanol; at 60 ℃; for 5h;

DOI:10.1021/ja00051a051

Reference yield:

<1R-(1α,2β,3α,4β,5β)>-5-Azido-2-(benzyloxy)-1-<(benzyloxy)methyl>-3,4-bis(methoxymethoxy)-1-cyclopentanol (144811-29-0) → (1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride (144811-35-8)

Guidance literature:

Multi-step reaction with 2 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

With hydrogenchloride; lithium aluminium tetrahydride; In methanol; diethyl ether;

DOI:10.1021/jo00083a023

Reference yield:

(1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride (144811-35-8) → 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 3 steps

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

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

3: Et₃N / acetonitrile / 1 h / 0 °C

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

DOI:10.1021/jo00083a023

upstream raw materials:

(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:

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

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

trehazolin

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