(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine

Base Information

• Chemical Name: (1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine
• CAS No.: 178271-99-3
• Molecular Formula: C₃₃H₄₁NO₅
• Molecular Weight: 531.692
• Mol file: 178271-99-3.mol

Synonyms:(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine

Chemical Property of (1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine

There total 4 articles about (1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine 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: 100.0%

(2R,3S,4R,5R,6S)-2-((1R,2R)-2-Azido-cyclohexyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran (178271-73-3) → (1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine (178271-99-3)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1016/0040-4039(96)01114-8

Reference yield:

(1R,2R)-trans-2-azidocyclohexanol (110716-78-4) → (1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine (178271-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / SnCl₂, AgClO₄, 4 A MS / CH₂Cl₂

2: 100 percent / LiAlH₄

With lithium aluminium tetrahydride; silver perchlorate; tin(ll) chloride; In dichloromethane;

DOI:10.1016/0040-4039(96)01114-8

Reference yield:

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite (153659-02-0) → (1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-Tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylamine (178271-99-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 4A molecular sieves, TfOH / CH₂Cl₂ / 1 h / -15 °C

2: 97 percent / water / benzene / 15 h / Heating

With trifluorormethanesulfonic acid; 4 A molecular sieve; water; In dichloromethane; benzene;

DOI:10.1021/ja952265x

upstream raw materials:

(2R,3S,4R,5R,6S)-2-((1R,2R)-2-Azido-cyclohexyloxy)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

(1R,2R)-trans-2-azidocyclohexanol

2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride

Dibenzyl 6-deoxy-2,3,4-tri-O-benzyl-β-L-galactopyranosyl phosphite

Downstream raw materials:

(S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester

4-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propylcarbamoyl}-butyric acid benzyl ester

N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-succinamic acid benzyl ester

{(4aR,6R,8R,8aR)-6-Methoxy-2-phenyl-6-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid methyl ester