4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

Base Information

• Chemical Name: 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine
• CAS No.: 236115-73-4
• Molecular Formula: C₄₀H₄₄N₆O₈
• Molecular Weight: 736.825
• Mol file: 236115-73-4.mol

Synonyms:4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

Chemical Property of 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine

There total 5 articles about 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine 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:

Acetic acid (1S,2S,3R,5S,6R)-2-acetoxy-3,5-diazido-6-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester → 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine (236115-73-4)

Guidance literature:

With sodium methylate; In tetrahydrofuran; methanol; for 16h; Yield given; Ambient temperature;

DOI:10.1021/ja9910356

Reference yield:

2-deoxystreptamine (2037-48-1,731753-11-0) → 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine (236115-73-4)

Guidance literature:

Multi-step reaction with 5 steps

1: TfN₃, Et₃N, CuSO₄ / CH₂Cl₂; methanol / 21 h / Ambient temperature

2: pyridine, DMAP / 23 h / Ambient temperature

3: 71 percent / Novozym 435 (Candida antarctica lipase), sodium phosphate buffer (pH 6.2) / toluene / 72 h / Ambient temperature

4: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -30 °C

5: NaOMe / tetrahydrofuran; methanol / 16 h / Ambient temperature

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium phosphate buffer; Novozym 435 (Candida antarctica lipase); triflic azide; sodium methylate; copper(II) sulfate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja9910356

Reference yield:

(1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol (90899-14-2) → 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-deoxystreptamine (236115-73-4)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine, DMAP / 23 h / Ambient temperature

2: 71 percent / Novozym 435 (Candida antarctica lipase), sodium phosphate buffer (pH 6.2) / toluene / 72 h / Ambient temperature

3: TfOH, NIS / diethyl ether; CH₂Cl₂ / 0.5 h / -30 °C

4: NaOMe / tetrahydrofuran; methanol / 16 h / Ambient temperature

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium phosphate buffer; Novozym 435 (Candida antarctica lipase); sodium methylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/ja9910356

upstream raw materials:

2-deoxystreptamine

(1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol-triacetat

(1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol

[(1S,2S,3R,4S,6R)-2-acetoxy-4,6-diazido-3-hydroxy-cyclohexyl] acetate

Downstream raw materials:

4-O-(α-D-glucopyranosyl)-2-deoxystreptamine