(R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol

Base Information

• Chemical Name: (R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol
• CAS No.: 119111-07-8
• Molecular Formula: C₂₈H₃₀O₅
• Molecular Weight: 446.543
• Mol file: 119111-07-8.mol

Synonyms:(R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol

Chemical Property of (R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol

There total 13 articles about (R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol 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: 79.0%

2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose (20770-84-7,113566-69-1,113566-70-4) + Methylenetriphenylphosphorane (19493-09-5) → (R)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-gluco-hept-1-enitol (119111-07-8)

Guidance literature:

With n-butyllithium; In 1,2-dimethoxyethane; hexane; at 45 ℃; for 2.33333h;

DOI:10.1016/j.bmc.2004.09.019

Reference yield:

D-galactose pentaacetate (25878-60-8) → (S)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-galacto-hept-1-enitol (119111-07-8,119111-35-2,119237-93-3)

Guidance literature:

Multi-step reaction with 6 steps

1: SnCl₄

2: AGMP resin / methanol

3: ZnCl₂

4: NaH / dimethylformamide

5: 2.) HgCl₂, H₂O / 1.) Ir(+)(COD)Ph₂PMe

6: 1.) n-BuLi / 1.) THF, hexane, -20 deg C --> room temp., 1h, 2.) -20 deg C --> room temp., 16h, 3.) 50 deg C, 15 min

With n-butyllithium; AGMP resin; water; tin(IV) chloride; sodium hydride; mercury dichloride; zinc(II) chloride; Ir(+)(COD)Ph₂PMe; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja00187a031

Reference yield:

benzyl bromide (100-39-0) → (S)-1,2-Dideoxy-3,4-bis-O-(phenylmethyl)-5,7-O-(phenylmethylene)-D-galacto-hept-1-enitol (119111-07-8,119111-35-2,119237-93-3)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / dimethylformamide

2: 2.) HgCl₂, H₂O / 1.) Ir(+)(COD)Ph₂PMe

3: 1.) n-BuLi / 1.) THF, hexane, -20 deg C --> room temp., 1h, 2.) -20 deg C --> room temp., 16h, 3.) 50 deg C, 15 min

With n-butyllithium; water; sodium hydride; mercury dichloride; Ir(+)(COD)Ph₂PMe; In N,N-dimethyl-formamide;

DOI:10.1021/ja00187a031

upstream raw materials:

2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose

Methylenetriphenylphosphorane

allyl 2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranoside

allyl 4,6-O-benzylidene-D-glucopyranoside

Downstream raw materials:

Imidazole-1-carbothioic acid O-[(2R,4R,5R)-4-((1R,2S)-1,2-bis-benzyloxy-but-3-enyl)-2-phenyl-[1,3]dioxan-5-yl] ester

<1R-(1α,2β,3α,4β,5β)>-1,5-Dimethyl-2,3,4-tris(phenylmethoxy)cyclopentane

<1S-(1α,2β,3α,4β,5α)>-2-Methyl-3,4,5-tris(phenylmethoxy)cyclopentanemethanol

<(2R)-(2α,4aβ,5β,6α,7β,7aβ)>-Hexahydro-5-methyl-2-phenyl-6,7-bis(phenylmethoxy)cyclopenta-1,3-dioxin