methyl-4-desoxy-4-<1D-(1N,2,4,5/3,6)-(5-C-hydroxymethyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-β-D-glucopyranoside

Base Information

• Chemical Name: methyl-4-desoxy-4-<1D-(1N,2,4,5/3,6)-(5-C-hydroxymethyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-β-D-glucopyranoside
• CAS No.: 122901-38-6
• Molecular Formula: C₁₄H₂₇NO₁₁
• Molecular Weight: 385.368
• Mol file: 122901-38-6.mol

Synonyms:

Chemical Property of methyl-4-desoxy-4-<1D-(1N,2,4,5/3,6)-(5-C-hydroxymethyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl-4-desoxy-4-<1D-(1N,2,4,5/3,6)-(5-C-hydroxymethyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-β-D-glucopyranoside

There total 9 articles about methyl-4-desoxy-4-<1D-(1N,2,4,5/3,6)-(5-C-hydroxymethyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-β-D-glucopyranoside 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: 63.0%

methyl-4-<1D-(1N,2,4,5/3,6)-(5-C-acetoxymethyl-2,3,4,6-tetra-O-acetyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-2,3,6-tri-O-acetyl-4-desoxy-β-D-glucopyranoside (122901-37-5) → methyl-4-desoxy-4-<1D-(1N,2,4,5/3,6)-(5-C-hydroxymethyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-β-D-glucopyranoside (122901-38-6)

Guidance literature:

With sodium methylate; In methanol; for 3h;

Reference yield:

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose (33208-46-7) → methyl-4-desoxy-4-<1D-(1N,2,4,5/3,6)-(5-C-hydroxymethyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-β-D-glucopyranoside (122901-38-6)

Guidance literature:

Multi-step reaction with 7 steps

1: propan-1-ol / 30 h / 90 °C

2: pyridine

3: 89 percent / BF₃-diethyl ether / 4 h / Ambient temperature

4: 157 mg / HBr / CH₂Cl₂ / 1 h / Ambient temperature

5: 53 percent / Ag₂CO₃, AgClO₄ / CH₂Cl₂; toluene / 5 h / -30 °C

6: 1) H₂, 2) pyridine / 1) Pd/C (10percent) / 1) CH₃OH, 1 atm, 24 h

7: 63 percent / 0.1 N CH₃ONa / methanol / 3 h

With pyridine; boron trifluoride diethyl etherate; hydrogen bromide; hydrogen; sodium methylate; silver perchlorate; silver carbonate; palladium on activated charcoal; In methanol; propan-1-ol; dichloromethane; toluene;

Reference yield:

1L-2-amino-1,4,5,6-tetra-O-benzyl-4-C-bezyloxymethyl-2-desoxy-muco-inosite (122901-18-2) → methyl-4-desoxy-4-<1D-(1N,2,4,5/3,6)-(5-C-hydroxymethyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-β-D-glucopyranoside (122901-38-6)

Guidance literature:

Multi-step reaction with 7 steps

1: propan-1-ol / 30 h / 90 °C

2: pyridine

3: 89 percent / BF₃-diethyl ether / 4 h / Ambient temperature

4: 157 mg / HBr / CH₂Cl₂ / 1 h / Ambient temperature

5: 53 percent / Ag₂CO₃, AgClO₄ / CH₂Cl₂; toluene / 5 h / -30 °C

6: 1) H₂, 2) pyridine / 1) Pd/C (10percent) / 1) CH₃OH, 1 atm, 24 h

7: 63 percent / 0.1 N CH₃ONa / methanol / 3 h

With pyridine; boron trifluoride diethyl etherate; hydrogen bromide; hydrogen; sodium methylate; silver perchlorate; silver carbonate; palladium on activated charcoal; In methanol; propan-1-ol; dichloromethane; toluene;

upstream raw materials:

methyl-4-<1D-(1N,2,4,5/3,6)-(5-C-acetoxymethyl-2,3,4,6-tetra-O-acetyl-2,3,4,5,6-pentahydroxycyclohexyl)amino>-2,3,6-tri-O-acetyl-4-desoxy-β-D-glucopyranoside

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose

1L-2-amino-1,4,5,6-tetra-O-benzyl-4-C-bezyloxymethyl-2-desoxy-muco-inosite

(1S,2S,3S,4R,5R)-4-Benzyloxy-2-((1S,2S,3R,4S,5R,6S)-3,4,5,6-tetrakis-benzyloxy-3-benzyloxymethyl-2-hydroxy-cyclohexylamino)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol