Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate

Base Information

Chemical Name:Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate
CAS No.:155307-29-2
Molecular Formula:C₄₀H₅₀O₇Si₂
Molecular Weight:699.004
Hs Code.:

Synonyms:Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate

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Chemical Property of Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate

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Technology Process of Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate

There total 6 articles about Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate 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: 59.0%

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

: 155307-29-2
Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate

Guidance literature:: With toluene-4-sulfonic acid; In methanol; for 4h;
DOI:10.1021/jo00089a045

Reference yield:

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

: 155307-29-2
Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate

Guidance literature:: Multi-step reaction with 6 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

6: 59 percent / p-toluenesulfonic acid / methanol / 4 h

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

Reference yield:

: 155307-25-8
(4R,5R,6R)-2-Bromo-3,4-(isopropylidenedioxy)-5-<(tert-butyldiphenylsilyl)oxy>-2-cyclohepten-1-one

: 155307-29-2
Methyl 3-deoxy-4,7-bis-O-(tert-butyldiphenylsilyl)-D-arabino-heptopyranosulosonate

Guidance literature:: Multi-step reaction with 5 steps

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

3: 80 percent / Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

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

5: 59 percent / p-toluenesulfonic acid / methanol / 4 h

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