1-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3-((1R,2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-hydroxymethyl-cyclopentyl)-thiourea

Base Information

• Chemical Name: 1-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3-((1R,2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-hydroxymethyl-cyclopentyl)-thiourea
• CAS No.: 211238-37-8
• Molecular Formula: C₃₅H₄₄N₂O₁₀S
• Molecular Weight: 684.808
• Mol file: 211238-37-8.mol

Synonyms:

Chemical Property of 1-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3-((1R,2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-hydroxymethyl-cyclopentyl)-thiourea

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3-((1R,2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-hydroxymethyl-cyclopentyl)-thiourea

There total 5 articles about 1-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3-((1R,2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-hydroxymethyl-cyclopentyl)-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: 97.0%

(1S,2S,3R,4S,5R)-5-Amino-1-hydroxymethyl-cyclopentane-1,2,3,4-tetraol + methyl 3,4,6-tri-O-benzyl-2-deoxy-2-isothiocyanato-α-D-glucopyranoside (211237-82-0) → 1-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3-((1R,2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-hydroxymethyl-cyclopentyl)-thiourea (211238-37-8)

Guidance literature:

In N,N-dimethyl-formamide; for 21h; Ambient temperature;

DOI:10.1016/S0008-6215(98)00045-7

Reference yield:

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose (55682-47-8) → 1-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3-((1R,2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-hydroxymethyl-cyclopentyl)-thiourea (211238-37-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 16 percent / HCl / 18 h / 60 °C

2: 93 percent / NaH / dimethylformamide / 3 h / Ambient temperature

3: H₂S / pyridine; H₂O / 7 h / Ambient temperature

4: 92.7 percent / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 97 percent / dimethylformamide / 21 h / Ambient temperature

With hydrogenchloride; hydrogen sulfide; sodium hydride; In pyridine; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00045-7

Reference yield:

methyl-2-azido-3,4,5-tri-O-benzyl-2-desoxy-α-D-glucopyranoside (95015-29-5) → 1-((2S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-3-((1R,2S,3S,4R,5S)-2,3,4,5-tetrahydroxy-2-hydroxymethyl-cyclopentyl)-thiourea (211238-37-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂S / pyridine; H₂O / 7 h / Ambient temperature

2: 92.7 percent / CH₂Cl₂ / 1.5 h / Ambient temperature

3: 97 percent / dimethylformamide / 21 h / Ambient temperature

With hydrogen sulfide; In pyridine; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00045-7

upstream raw materials:

methyl 3,4,6-tri-O-benzyl-2-deoxy-2-isothiocyanato-α-D-glucopyranoside

1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose

methyl-2-azido-3,4,5-tri-O-benzyl-2-desoxy-α-D-glucopyranoside

Methyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranoside