ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside
CAS No.:1607445-07-7
Molecular Formula:C₂₈H₃₂O₆S
Molecular Weight:496.624
Hs Code.:

Synonyms:ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

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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 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

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Technology Process of ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

There total 2 articles about ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside 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: 94.0%

: 1607445-06-6
ethyl 4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

: 75-36-5
acetyl chloride

: 1607445-07-7
ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With 2,4,6-trimethyl-pyridine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.carres.2014.01.022

Reference yield:

: C₂₆H₂₈O₅S

: 1607445-07-7
ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate; di-n-butylboryl trifluoromethanesulfonate / dichloromethane; tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2: 2,4,6-trimethyl-pyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

With 2,4,6-trimethyl-pyridine; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.carres.2014.01.022

Reference yield: 67.0%

: 1607445-07-7
ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

: 1607445-15-7
benzyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranoside)uronate

: 1607445-16-8
ethyl [benzyl (3-O-benzyl-2,4-O-di-tert-butylsilylene-β-D-glucopyranosyl)uronate]-(1→2)-6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: benzyl (phenyl 3-O-benzyl-2,4-O-di-tert-butylsilylene-1-thio-β-D-glucopyranoside)uronate; With Thiobenzophenon; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; toluene; at -60 ℃; for 0.333333h; Molecular sieve;

ethyl 6-O-acetyl-4-O-benzyl-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside; With trifluoromethylsulfonic anhydride; In dichloromethane; toluene; at -60 - 0 ℃; for 2.16h; Molecular sieve;
DOI:10.1016/j.carres.2014.01.022