Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester
• CAS No.: 144985-21-7
• Molecular Formula: C₂₅H₂₉ClO₆
• Molecular Weight: 460.955

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester

There total 8 articles about Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester 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:

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester (144985-21-7)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOMe / methanol; tetrahydrofuran

2: 1) Bu₂SnO, 2) Bu₄NBr / 1) THF, toluene, 2) THF

3: TsOH*H₂O / tetrahydrofuran

4: DMAP, pyridine

5: 1) NaBH₃CN, powdered molecular sieves 4A, HCl, 2) NaH / 1) THF, 2) DMF

7: CCl₄, (Me₂N)3P / THF

With pyridine; hydrogenchloride; tetrachloromethane; dmap; 4 A molecular sieve; tetrabutylammomium bromide; sodium methylate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; toluene-4-sulfonic acid; Hexamethylphosphorous triamide; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)61200-5

Reference yield:

p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside (144985-19-3) → Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester (144985-21-7)

Guidance literature:

Multi-step reaction with 5 steps

1: TsOH*H₂O / tetrahydrofuran

2: DMAP, pyridine

3: 1) NaBH₃CN, powdered molecular sieves 4A, HCl, 2) NaH / 1) THF, 2) DMF

5: CCl₄, (Me₂N)3P / THF

With pyridine; hydrogenchloride; tetrachloromethane; dmap; 4 A molecular sieve; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; Hexamethylphosphorous triamide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)61200-5

Reference yield:

4-methoxyphenyl β-D-galactopyranoside (3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9) → Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-chloro-tetrahydro-pyran-3-yl ester (144985-21-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) Bu₂SnO, 2) Bu₄NBr / 1) THF, toluene, 2) THF

2: TsOH*H₂O / tetrahydrofuran

3: DMAP, pyridine

4: 1) NaBH₃CN, powdered molecular sieves 4A, HCl, 2) NaH / 1) THF, 2) DMF

6: CCl₄, (Me₂N)3P / THF

With pyridine; hydrogenchloride; tetrachloromethane; dmap; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; toluene-4-sulfonic acid; Hexamethylphosphorous triamide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)61200-5

upstream raw materials:

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside

4-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-galactopyranoside

Acetic acid (2S,3R,4S,5S,6R)-4-allyloxy-6-benzyloxymethyl-5-hydroxy-2-(4-methoxy-phenoxy)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3R,4S,5S,6R)-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester

2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2R,3R,4S,5S,6R)-3-acetoxy-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester

2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-3-acetoxy-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester

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