4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside

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Chemical Name:4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside
CAS No.:407616-99-3
Molecular Formula:C₅₄H₈₄O₁₁Si
Molecular Weight:937.34
Hs Code.:

Synonyms:4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside

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Chemical Property of 4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside

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Technology Process of 4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside

There total 10 articles about 4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-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: 93.0%

: 108-24-7
acetic anhydride

: 407616-98-2
4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 2,3-di-O-dodecanoyl-β-D-mannopyranoside

: 407616-99-3
4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside

Guidance literature:: With pyridine; at 20 ℃; for 4h;
DOI:10.1016/S0040-4020(01)01087-0

Reference yield:

: 87770-83-0
(Z)-4-((tert-butyldiphenylsilyl)oxy)but-2-en-1-ol

: 407616-99-3
4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; 3 Angstroem molecular sieves / triflic anhydride / CH₂Cl₂ / 0.08 h / -60 °C

1.2: 84 percent / CH₂Cl₂ / -60 - 20 °C

2.1: 65 percent / (o-biphenyl)P(tBu)2; potassium tert-butoxide / Pd₂(dba)3 / toluene / 5 h / 70 °C

3.1: 84 percent / SnCl₄ / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 98 percent / DMAP; pyridine / CH₂Cl₂ / 5 h / 20 °C

5.1: 51 percent / iodine / methanol / 3 h / 70 °C

6.1: 93 percent / pyridine / 4 h / 20 °C

With pyridine; dmap; 1-benzenesulfinyl piperidine; 3 A molecular sieve; potassium tert-butylate; iodine; tin(IV) chloride; johnphos; 2,4,6-tri-tert-butylpyrimidine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifluoromethylsulfonic anhydride; In methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)01087-0

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 407616-99-3
4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 81 percent / NaH / diethyl ether / 3 h / 20 °C

2.1: 1-(benzenesulfinyl)piperidine; 2,4,6-tri-tert-butylpyrimidine; 3 Angstroem molecular sieves / triflic anhydride / CH₂Cl₂ / 0.08 h / -60 °C

2.2: 84 percent / CH₂Cl₂ / -60 - 20 °C

3.1: 65 percent / (o-biphenyl)P(tBu)2; potassium tert-butoxide / Pd₂(dba)3 / toluene / 5 h / 70 °C

4.1: 84 percent / SnCl₄ / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 98 percent / DMAP; pyridine / CH₂Cl₂ / 5 h / 20 °C

6.1: 51 percent / iodine / methanol / 3 h / 70 °C

7.1: 93 percent / pyridine / 4 h / 20 °C

With pyridine; dmap; 1-benzenesulfinyl piperidine; 3 A molecular sieve; potassium tert-butylate; iodine; tin(IV) chloride; sodium hydride; johnphos; 2,4,6-tri-tert-butylpyrimidine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; trifluoromethylsulfonic anhydride; In methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)01087-0