4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside

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Chemical Name:4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside
CAS No.:1441884-85-0
Molecular Formula:C₃₃H₄₈N₂O₁₂Si
Molecular Weight:692.836
Hs Code.:

Synonyms:4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside

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Chemical Property of 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside

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Technology Process of 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside

There total 6 articles about 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside 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: 60.0%

: 1441884-89-4
C₃₃H₄₉BrO₁₂Si

: 1441884-85-0
4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside

Guidance literature:: With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; Inert atmosphere;
DOI:10.1002/chem.201203725

Reference yield:

: 530-26-7
D-Mannose

: 1441884-85-0
4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: acetic anhydride; iodine / 20 °C

1.2: 0 - 20 °C

1.3: 20 °C

2.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 50 °C / 76.01 Torr

3.1: di(n-butyl)tin oxide / toluene / 2 h / 110 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

4.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.1: trifluorormethanesulfonic acid; N-iodo-succinimide / dichloromethane / 2 h / -20 °C / Molecular sieve; Inert atmosphere

6.1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C / Inert atmosphere

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; N,N'-ditosylhydrazine; camphor-10-sulfonic acid; iodine; acetic anhydride; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.201203725

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0
(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 1441884-85-0
4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-α-D-mannopyranoside-(1→6)-1,2-3,4-diisopropylidene-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 50 °C / 76.01 Torr

2.1: di(n-butyl)tin oxide / toluene / 2 h / 110 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

4.1: trifluorormethanesulfonic acid; N-iodo-succinimide / dichloromethane / 2 h / -20 °C / Molecular sieve; Inert atmosphere

5.1: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C / Inert atmosphere

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; N,N'-ditosylhydrazine; camphor-10-sulfonic acid; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.201203725