methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-glucopyranoside

Base Information

Chemical Name:methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-glucopyranoside
CAS No.:142644-83-5
Molecular Formula:C₂₂H₂₆O₆
Molecular Weight:386.445
Hs Code.:

Synonyms:methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-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 methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-glucopyranoside

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Technology Process of methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-glucopyranoside

There total 14 articles about methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-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: 92.0%

: 942041-43-2
C₂₂H₂₄O₆

: 142644-83-5
methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-glucopyranoside

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at 0 ℃; for 0.166667h;
DOI:10.1016/j.tetlet.2007.03.031

Reference yield:

: 942041-32-9
C₂₀H₂₆O₆

: 142644-83-5
methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / AcOH; water / tetrahydrofuran / 1 h / 50 °C

2.1: 89 percent / NaH / dimethylformamide / 1 h / 20 °C

3.1: BH₃*Me₃S; NaOH; H₂O₂ / tetrahydrofuran / 24 h

3.2: oxalyl chloride; DMSO / CH₂Cl₂ / 4 h / -78 °C

4.1: 94 percent / Et₃N / CH₂Cl₂ / 168 h / 20 °C

5.1: 92 percent / NaBH₄ / ethanol; tetrahydrofuran / 0.17 h / 0 °C

With sodium hydroxide; sodium tetrahydroborate; water; dihydrogen peroxide; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.03.031

Reference yield:

: 50680-08-5
(4aR,6S,8S,8aR)-6-Methoxy-2-phenyl-8-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one

: 142644-83-5
methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-hydroxymethyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

2.1: 91 percent / AcOH; water / tetrahydrofuran / 1 h / 50 °C

3.1: 89 percent / NaH / dimethylformamide / 1 h / 20 °C

4.1: BH₃*Me₃S; NaOH; H₂O₂ / tetrahydrofuran / 24 h

4.2: oxalyl chloride; DMSO / CH₂Cl₂ / 4 h / -78 °C

5.1: 94 percent / Et₃N / CH₂Cl₂ / 168 h / 20 °C

6.1: 92 percent / NaBH₄ / ethanol; tetrahydrofuran / 0.17 h / 0 °C

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; water; dihydrogen peroxide; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig reaction;
DOI:10.1016/j.tetlet.2007.03.031