ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside
CAS No.:872333-46-5
Molecular Formula:C₁₇H₂₂BrN₃O₄S
Molecular Weight:444.349
Hs Code.:

Synonyms:ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside

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Technology Process of ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside

There total 4 articles about ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-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: 70.0%

: 861819-33-2
ethyl 4-azido-3-O-benzyl-4,6-dideoxy-1-thio-β-D-glucopyranoside

: 598-21-0
2-Bromoacetyl bromide

: 872333-46-5
ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside

Guidance literature:: With tetramethylurea; In dichloromethane;
DOI:10.1016/j.carres.2005.09.015

Reference yield: 62.0%

: 876345-23-2
1-O-acetyl-4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-D-glucopyranoside

: 75-08-1
ethanethiol

: 872333-46-5
ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside

: ethyl 4-azido-3-O-benzyl-2-O-bromoacetyl-4,6-dideoxy-1-thio-α-D-glucopyranoside

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1016/j.bmcl.2005.10.056

Reference yield:

: 861819-27-4
methyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-glucopyranoside

: 872333-46-5
ethyl 4-azido-3-O-benzyl-2-O-(bromoacetyl)-4,6-dideoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / TMU / CH₂Cl₂ / 0 - 20 °C

2: 93 percent / H₂SO₄; AcOH / 1 h / 20 °C

3: 62 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 20 °C

With sulfuric acid; boron trifluoride diethyl etherate; acetic acid; tetramethylurea; In dichloromethane;
DOI:10.1016/j.bmcl.2005.10.056