Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate

Base Information

Chemical Name:Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate
CAS No.:155307-28-1
Molecular Formula:C₄₃H₅₄O₇Si₂
Molecular Weight:739.069
Hs Code.:

Synonyms:Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate

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Chemical Property of Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate

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Technology Process of Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate

There total 5 articles about Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate 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: 86.0%

: (R)-4-(tert-Butyl-diphenyl-silanyloxy)-4-[(4R,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-hydroxy-butyric acid methyl ester

: 155307-28-1
Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate

Guidance literature:: With dipyridinium dichromate; 4 A molecular sieve; In dichloromethane; for 16h;
DOI:10.1021/jo00089a045

Reference yield:

: 151936-92-4
(4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one

: 155307-28-1
Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / Br₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

2: 90 percent / NaBH₄, CeCl₃*7H₂O / methanol / 1.) r.t., 10 min, 2.) -78 deg C, 15 min

4: 80 percent / Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

5: 86 percent / pyridinium dichromate, molecular sieves 4 Angstroem / CH₂Cl₂ / 16 h

With sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; 4 A molecular sieve; bromine; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jo00089a045

Reference yield:

: 1052112-69-2
(3aR,4R,8aR)-7-Bromo-4-(tert-butyl-diphenyl-silanyloxy)-2,2-dimethyl-4,5,6,8a-tetrahydro-3aH-cyclohepta[1,3]dioxol-6-ol

: 155307-28-1
Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-5,6-O-isopropylidene-D-arabino-heptulosonate

Guidance literature:: Multi-step reaction with 3 steps

2: 80 percent / Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

3: 86 percent / pyridinium dichromate, molecular sieves 4 Angstroem / CH₂Cl₂ / 16 h

With dipyridinium dichromate; 4 A molecular sieve; triethylamine; In dichloromethane;
DOI:10.1021/jo00089a045