allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranoside

Base Information

Chemical Name:allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranoside
CAS No.:915150-33-3
Molecular Formula:C₃₉H₅₂O₇Si
Molecular Weight:660.923
Hs Code.:

Synonyms:allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-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 allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranoside

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Technology Process of allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranoside

There total 13 articles about allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-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: 80.0%

: 883878-61-3
1-O-[2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranosyl] trichloroacetimidate

: 107-18-6
allyl alcohol

: 915150-33-3
allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranoside

: allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-β-D-mannopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo061233x

Reference yield:

: 883878-96-4
3,4-di-O-benzyl-1,2-O-(α-methoxybenzylidene)-6-O-(triisopropylsilyl)-β-D-mannopyranose

: 107-18-6
allyl alcohol

: 915150-33-3
allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranoside

Guidance literature:: With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ja0565368

Reference yield:

: 14218-11-2,14218-30-5,61198-88-7,108438-33-1,108836-02-8,114682-36-9,127305-34-4,151377-77-4
2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide

: 915150-33-3
allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 2,6-lutidine / CH₂Cl₂ / 72 h / 20 °C

2: 2.40 g / NaOMe / methanol / 24 h / 24 °C

3: 66 percent / imidazole / dimethylformamide / 0 - 20 °C

4: 95 percent / imidazole; NaH / dimethylformamide / 0 - 20 °C

5: acetic acid / tetrahydrofuran / 4 h / 20 °C

6: 2.53 g / DBU / CH₂Cl₂ / 0.25 h / 0 °C

7: 80 percent / TMSOTf / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo061233x