methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside

Base Information

Chemical Name:methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside
CAS No.:82731-51-9
Molecular Formula:C₂₆H₃₆O₆Si
Molecular Weight:472.654
Hs Code.:

Synonyms:methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside

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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 methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside

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Technology Process of methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside

There total 5 articles about methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside 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: 88.0%

: Acetic acid (2R,3S,4S,5R,6S)-3-hydroxy-2-hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-4-yl ester

: 58479-61-1
tert-butylchlorodiphenylsilane

: 82731-51-9
methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside

Guidance literature:: In pyridine; at 0 ℃;
DOI:10.1016/S0040-4020(01)82415-7

Reference yield:

: 75879-81-1
Methyl 4,6-O-Benzylidene-2-deoxy-2-C-methyl-α-D-allopyranoside

: 82731-51-9
methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 91 percent / DMAP / CH₂Cl₂

2: aq. 50percent AcOH

3: pyridine / 18 h / 0 °C

With pyridine; dmap; acetic acid; In dichloromethane;
DOI:10.1021/ja00386a076

Reference yield:

: 19465-06-6
methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

: 82731-51-9
methyl 3-O-acetyl-6-O-t-butyldiphenylsilyl-2-deoxy-C-methyl-α-D-allopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / Ac₂O / dimethylsulfoxide / Ambient temperature

2: 85 percent / NaOMe / methanol / 4 h / 0 °C

3: 96 percent / sodium borohydride / dimethylformamide; methanol / 1.5 h

4: 91 percent / N,N-dimethylaminopyridine / CH₂Cl₂; pyridine

5: AcOH / H₂O / 15 h

6: 88 percent / pyridine / 0 °C

With dmap; sodium tetrahydroborate; sodium methylate; acetic anhydride; acetic acid; In pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)82415-7