2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid

Base Information

Chemical Name:2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid
CAS No.:190910-35-1
Molecular Formula:C₃₃H₄₄O₆Si
Molecular Weight:564.794
Hs Code.:

Synonyms:2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid

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Chemical Property of 2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid

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Technology Process of 2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid

There total 14 articles about 2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid 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: 97.0%

: 190910-32-8
2,3,6-tri-O-benzyl4-deoxy-5-O-(tert-butyldiphenylsilyl)-D-xylo-hexose

: 190910-35-1
2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid

Guidance literature:: With sodium dihydrogenphosphate; 2-Methyl-1-butene; In water; tert-butyl alcohol; for 3h;
DOI:10.1021/jo970067d

Reference yield:

: 3162-96-7
methyl 4,6-O-benzylidene-α-D-glucopyranoside

: 190910-35-1
2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / NaH / dimethylformamide

2: 84 percent / NaBNBH₃, HCl / diethyl ether

3: 85 percent / pyridine

4: 98 percent / NaBH₄ / acetonitrile

5: 66 percent / HOAc, HCl

6: 70 percent / p-TsOH*H₂O / ethanol / 3 h / Heating

7: 88 percent / pyridine

8: 1.) O₃, 2.) Me₂S / 1.) AcOEt, -78 deg C, 1 h

9: 97 percent / NaH₂PO₄, 2-methyl-1-butene, NaOCl₂ / 2-methyl-propan-2-ol; H₂O / 3 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium dihydrogenphosphate; dimethylsulfide; NaBNBH₃; sodium hydride; toluene-4-sulfonic acid; ozone; 2-Methyl-1-butene; acetic acid; In diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo970067d

Reference yield:

: 7177-79-9,13035-24-0,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9,13225-19-9
methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

: 190910-35-1
2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / NaBNBH₃, HCl / diethyl ether

2: 85 percent / pyridine

3: 98 percent / NaBH₄ / acetonitrile

4: 66 percent / HOAc, HCl

5: 70 percent / p-TsOH*H₂O / ethanol / 3 h / Heating

6: 88 percent / pyridine

7: 1.) O₃, 2.) Me₂S / 1.) AcOEt, -78 deg C, 1 h

8: 97 percent / NaH₂PO₄, 2-methyl-1-butene, NaOCl₂ / 2-methyl-propan-2-ol; H₂O / 3 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium dihydrogenphosphate; dimethylsulfide; NaBNBH₃; toluene-4-sulfonic acid; ozone; 2-Methyl-1-butene; acetic acid; In diethyl ether; ethanol; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo970067d