pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside

Base Information

Chemical Name:pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside
CAS No.:866885-38-3
Molecular Formula:C₄₈H₅₄O₉Si
Molecular Weight:803.037
Hs Code.:

Synonyms:pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside

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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 pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside

There total 8 articles about pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-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: 70.0%

: 866885-37-2
dibutyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranosyl phosphate

: 821-09-0
n-Pent-4-enyl alcohol

: 866885-38-3
pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside

Guidance literature:: With t-butyldimethylsiyl triflate; In dichloromethane; at -78 - -30 ℃; for 3h;
DOI:10.1081/CAR-200067008

Reference yield:

: 866885-19-0
dimethyl(2-naphthylmethyl)vinylsilane

: 866885-38-3
pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C

1.2: 58 percent / hydrogen peroxide; sodium hydroxide / ethanol; H₂O / 1 h / Heating

2.1: 63 percent / diethyl ether; toluene / 2.5 h / -15 - 20 °C

3.1: 98 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / 20 °C

4.1: dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

5.1: CH₂Cl₂ / 0.5 h / -78 °C

6.1: 0.290 g / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

7.1: 70 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h / -78 - -30 °C

With dmap; t-butyldimethylsiyl triflate; 3,3-dimethyldioxirane; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; toluene;
DOI:10.1081/CAR-200067008

Reference yield:

: 866885-20-3
2-[dimethyl(2-naphthylmethyl)silyl]ethanol

: 866885-38-3
pent-4-enyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-{2-[dimethyl(2-naphthylmethyl)silyl]ethoxycarbonyl}-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 63 percent / diethyl ether; toluene / 2.5 h / -15 - 20 °C

2: 98 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 15 h / 20 °C

3: dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

4: CH₂Cl₂ / 0.5 h / -78 °C

5: 0.290 g / 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

6: 70 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 3 h / -78 - -30 °C

With dmap; t-butyldimethylsiyl triflate; 3,3-dimethyldioxirane; In diethyl ether; dichloromethane; acetone; toluene;
DOI:10.1081/CAR-200067008