4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside

Base Information

Chemical Name:4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside
CAS No.:429679-60-7
Molecular Formula:C₆₃H₈₂O₁₂Si
Molecular Weight:1059.42
Hs Code.:

Synonyms:4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside

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Chemical Property of 4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside

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Technology Process of 4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside

There total 9 articles about 4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside 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: 99.0%

: 108869-64-3,130177-78-5,129163-12-8
2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

: 429679-59-4
4-pentenyl 2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannopyranoside

: 429679-60-7
4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside

Guidance literature:: With t-butyldimethylsiyl triflate; In dichloromethane; at -20 ℃; for 0.5h;
DOI:10.1002/1099-0690(200203)2002:5<826::AID-EJOC826>3.0.CO;2-2

Reference yield:

: 100-39-0
benzyl bromide

: 429679-60-7
4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 93 percent / sodium hydride / dimethylformamide / 2 h / 20 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.25 h / 0 °C

2.2: 87 percent / ZnCl₂ / diethyl ether; CH₂Cl₂ / 16 h / 20 °C

3.1: DMSO; Ac₂O / toluene / 48 h / 20 °C

4.1: NaBH₄ / CH₂Cl₂; methanol / 16 h / 20 °C

5.1: 98 percent / sodium hydride / toluene; dimethylformamide / 2 h / 20 °C

6.1: 92 percent / Pd₂dba3; (o-biphenyl)P(t-Bu)2; NaOtBu / toluene / 18 h / 80 °C

7.1: 90 percent / dichloroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 99 percent / TBDMSOTf / CH₂Cl₂ / 0.5 h / -20 °C

With dichloro-acetic acid; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-butyldimethylsiyl triflate; 3,3-dimethyldioxirane; acetic anhydride; sodium hydride; dimethyl sulfoxide; johnphos; sodium t-butanolate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/1099-0690(200203)2002:5<826::AID-EJOC826>3.0.CO;2-2

Reference yield:

: 294637-61-9
1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

: 429679-60-7
4-pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)-2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannospyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 93 percent / sodium hydride / dimethylformamide / 2 h / 20 °C

2.1: dimethyldioxirane / CH₂Cl₂; acetone / 0.25 h / 0 °C

2.2: 87 percent / ZnCl₂ / diethyl ether; CH₂Cl₂ / 16 h / 20 °C

3.1: DMSO; Ac₂O / toluene / 48 h / 20 °C

4.1: NaBH₄ / CH₂Cl₂; methanol / 16 h / 20 °C

5.1: 98 percent / sodium hydride / toluene; dimethylformamide / 2 h / 20 °C

6.1: 92 percent / Pd₂dba3; (o-biphenyl)P(t-Bu)2; NaOtBu / toluene / 18 h / 80 °C

7.1: 90 percent / dichloroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

8.1: 99 percent / TBDMSOTf / CH₂Cl₂ / 0.5 h / -20 °C

With dichloro-acetic acid; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-butyldimethylsiyl triflate; 3,3-dimethyldioxirane; acetic anhydride; sodium hydride; dimethyl sulfoxide; johnphos; sodium t-butanolate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1002/1099-0690(200203)2002:5<826::AID-EJOC826>3.0.CO;2-2