phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
CAS No.:434286-39-2
Molecular Formula:C₃₄H₄₁NO₇SSi
Molecular Weight:635.854
Hs Code.:

Synonyms:phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 8 articles about phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-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: 96.0%

: 791790-08-4
phenyl 3-O-(tert-butyldimethylsilyl)-4,6-O-(p-methoxybenzylidene)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

: 434286-39-2
phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: With borane-THF; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at 0 ℃; for 4h;
DOI:10.1055/s-2002-20962

Reference yield:

: 85-44-9
phthalic anhydride

: 434286-39-2
phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: NaOMe; Et₃N / methanol / 24.75 h

2: pyridine / 48 h / 20 °C

3: 76 percent / TMSOTf / CH₂Cl₂ / 7 h / 20 °C

4: NaOMe / methanol; CH₂Cl₂ / 2 h / -10 °C

5: 6.75 g / camphorsulfonic acid / toluene / 3 h / 90 °C

6: 88 percent / Et₃N; AgNO₃ / CH₂Cl₂ / 18 h / 20 °C

7: 96 percent / BH₃*THF; TMSOTf / CH₂Cl₂; tetrahydrofuran / 4 h / 0 °C

With pyridine; borane-THF; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; silver nitrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1055/s-2002-20962

Reference yield:

: 10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

: 434286-39-2
phenyl 3-O-(tert-butyldimethylsilyl)-4-O-(p-methoxybenzyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / TMSOTf / CH₂Cl₂ / 7 h / 20 °C

2: NaOMe / methanol; CH₂Cl₂ / 2 h / -10 °C

3: 6.75 g / camphorsulfonic acid / toluene / 3 h / 90 °C

4: 88 percent / Et₃N; AgNO₃ / CH₂Cl₂ / 18 h / 20 °C

5: 96 percent / BH₃*THF; TMSOTf / CH₂Cl₂; tetrahydrofuran / 4 h / 0 °C

With borane-THF; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; silver nitrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1055/s-2002-20962