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

Base Information

• Chemical Name: 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
• CAS No.: 144811-36-9
• Molecular Formula: C₅₅H₆₀N₂O₁₀S
• Molecular Weight: 941.155
• Mol file: 144811-36-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 3 articles about 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 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) → 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 (144811-36-9)

Guidance literature:

Multi-step reaction with 2 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

With hydrogenchloride; triethylamine; In tetrahydrofuran; methanol;

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) → 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 (144811-36-9)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1021/jo00083a023

Reference yield:

2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl isothiocyanate (93173-26-3) + (1R,2S,3R,4R,5S)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol; hydrochloride (144811-35-8) → 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 (144811-36-9)

Guidance literature:

With triethylamine; for 18h; Yield given; Ambient temperature;

DOI:10.1021/ja00051a051

upstream raw materials:

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

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

(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:

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

trehazolin