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

Base Information

• Chemical Name: Methyl-2,4,4¹-tri-O-benzyl-3-deoxy-4-C-(D-glycero-4¹-hydroxyethyl)-β-D-xylo-hexopyranoside
• CAS No.: 122927-15-5
• Molecular Formula: C₃₀H₃₆O₆
• Molecular Weight: 492.612

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

Chemical Property of Methyl-2,4,4¹-tri-O-benzyl-3-deoxy-4-C-(D-glycero-4¹-hydroxyethyl)-β-D-xylo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl-2,4,4¹-tri-O-benzyl-3-deoxy-4-C-(D-glycero-4¹-hydroxyethyl)-β-D-xylo-hexopyranoside

There total 28 articles about Methyl-2,4,4¹-tri-O-benzyl-3-deoxy-4-C-(D-glycero-4¹-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: 98.0%

Acetic acid (2R,3S,5R,6R)-3,5-bis-benzyloxy-3-((R)-1-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (122927-17-7) → Methyl-2,4,41-tri-O-benzyl-3-deoxy-4-C-(D-glycero-41-hydroxyethyl)-β-D-xylo-hexopyranoside (122927-15-5)

Guidance literature:

With triethylamine; In methanol; at 60 ℃;

DOI:10.1016/S0008-6215(00)90496-8

Reference yield:

benzyl chloride (100-44-7) → Methyl-2,4,41-tri-O-benzyl-3-deoxy-4-C-(D-glycero-41-hydroxyethyl)-α-und β-D-xylo-hexopyranoside (122927-12-2,122927-13-3,122927-14-4,122927-15-5)

Guidance literature:

Multi-step reaction with 8 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

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; oxalyl dichloride; sulfuric acid; dimsylsodium; sodium acetate; sodium hydride; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium dichloride; In methanol; water; acetic acid; acetone;

DOI:10.1016/S0008-6215(00)90496-8

Reference yield:

benzyl chloride (100-44-7) → Methyl-2,4,41-tri-O-benzyl-3-deoxy-4-C-(D-glycero-41-hydroxyethyl)-β-D-xylo-hexopyranoside (122927-15-5)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; hydrogenchloride; sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; oxalyl dichloride; sulfuric acid; dimsylsodium; sodium acetate; sodium hydride; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium dichloride; In methanol; water; acetic acid; acetone;

DOI:10.1016/S0008-6215(00)90496-8

upstream raw materials:

methanol

1,6-Anhydro-2,4,4'-tri-O-benzyl-3-deoxy-4-C-(D-glycero-4'-hydroxyethyl)-β-D-xylo-hexopyranose

benzyl chloride

4-O-Allyl-1,6-anhydro-2-O-tosyl-β-D-glucopyranose

Downstream raw materials:

Acetic acid (2R,3S,5R,6S)-3,5-bis-benzyloxy-3-((R)-1-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Acetic acid (2R,3S,5R,6R)-3,5-bis-benzyloxy-3-((R)-1-benzyloxy-ethyl)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Methyl-2,4,4'-tri-O-benzyl-3-deoxy-4-C-(D-glycero-4'-hydroxyethyl)-α-D-xylo-hexopyranoside

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

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