Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside

Base Information

Chemical Name:Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside
CAS No.:122927-25-7
Molecular Formula:C₃₀H₃₅BrO₅
Molecular Weight:555.509
Hs Code.:

Synonyms:Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside

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Chemical Property of Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside

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Technology Process of Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside

There total 16 articles about Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside 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: 83.0%

: 122927-15-5
Methyl-2,4,4¹-tri-O-benzyl-3-deoxy-4-C-(D-glycero-4¹-hydroxyethyl)-β-D-xylo-hexopyranoside

: 122927-25-7
Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside

Guidance literature:: With carbon tetrabromide; trimethylphosphane; In pyridine; at 60 ℃;
DOI:10.1016/S0008-6215(00)90496-8

Reference yield:

: 100-44-7
benzyl chloride

: 122927-25-7
Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 1) 1.4 M Na-methylsulfinylmethanide / 1) methyl sulfoxide, 0.5 h, 2) 1 h

2: 80 percent / PdCl₂, Na-acetate / acetic acid; H₂O / Ambient temperature

3: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -65 deg C, 15 min.

4: 1) BuLi / 1) oxolane, hexane, 2.5 h, 2) oxolane, -70 deg C, 3 h

5: 91 percent / HgCl₂, CdCO₃ / acetone; H₂O / 8 h / Heating

6: 54.6 percent / NaBH₄ / methanol / 0.5 h

7: 1) NaH / 1) DMF, 40 min., 2) 1 h

8: 1) conc. H₂SO₄, 2) 1percent HCl / 1) acetic anhydride, 0 deg C, 2) reflux

9: pyridine / 3 h / 20 °C

10: 98 percent / Et₃N / methanol / 60 °C

11: 83 percent / CBr₄, trimethylphosphine / pyridine / 60 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; oxalyl dichloride; carbon tetrabromide; sulfuric acid; dimsylsodium; sodium acetate; sodium hydride; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium dichloride; trimethylphosphane; In pyridine; methanol; water; acetic acid; acetone;
DOI:10.1016/S0008-6215(00)90496-8

Reference yield:

: 39697-97-7
4-O-Allyl-1,6-anhydro-2-O-tosyl-β-D-glucopyranose

: 122927-25-7
Methyl 2,4,4'-tri-O-benzyl-6-bromo-3,6-dideoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranoside

Guidance literature:: Multi-step reaction with 14 steps

1: 75 percent / Et₃N / CH₂Cl₂ / 0.33 h / -15 °C

2: 90 percent / 2M NaOMe / CH₂Cl₂; methanol / 20 h / 20 °C

3: 95 percent / LiAlH₄ / diethyl ether / 2 h / Heating

4: 1) 1.4 M Na-methylsulfinylmethanide / 1) methyl sulfoxide, 0.5 h, 2) 1 h

5: 80 percent / PdCl₂, Na-acetate / acetic acid; H₂O / Ambient temperature

6: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -65 deg C, 15 min.

7: 1) BuLi / 1) oxolane, hexane, 2.5 h, 2) oxolane, -70 deg C, 3 h

8: 91 percent / HgCl₂, CdCO₃ / acetone; H₂O / 8 h / Heating

9: 54.6 percent / NaBH₄ / methanol / 0.5 h

10: 1) NaH / 1) DMF, 40 min., 2) 1 h

11: 1) conc. H₂SO₄, 2) 1percent HCl / 1) acetic anhydride, 0 deg C, 2) reflux

12: pyridine / 3 h / 20 °C

13: 98 percent / Et₃N / methanol / 60 °C

14: 83 percent / CBr₄, trimethylphosphine / pyridine / 60 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cadmium(II) carbonate; oxalyl dichloride; carbon tetrabromide; sulfuric acid; dimsylsodium; sodium methylate; sodium acetate; sodium hydride; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium dichloride; trimethylphosphane; In pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; acetone;
DOI:10.1016/S0008-6215(00)90496-8