Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester
CAS No.:178621-86-8
Molecular Formula:C₄₃H₄₈O₁₁
Molecular Weight:740.848
Hs Code.:

Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

Synonyms:Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

There total 7 articles about Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-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: 87.1%

: 178621-79-9
Benzoic acid (2R,3S,5R,6S)-5-benzyloxy-6-methoxy-2-trimethylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

: Acetic acid (3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yl ester

: 178621-86-8
Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: With silver perchlorate; tin(IV) chloride; In diethyl ether; n-heptane; at 0 ℃; for 24h;
DOI:10.1016/0008-6215(96)00005-5

Reference yield:

: 98-88-4
benzoyl chloride

: 178621-86-8
Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 93.3 percent / pyridine / Ambient temperature

2: 94.4 percent / 5percent HCl in MeOH / toluene / 2 h / Ambient temperature

3: 93 percent / imidazole / CH₂Cl₂

4: 87.1 percent / tin(IV) chloride, silver perchlorate / heptane; diethyl ether / 24 h / 0 °C

With pyridine; 1H-imidazole; hydrogenchloride; silver perchlorate; tin(IV) chloride; In diethyl ether; n-heptane; dichloromethane; toluene;
DOI:10.1016/0008-6215(96)00005-5

Reference yield:

: 50272-14-5
methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-α-D-ribo-hexopyranoside

: 178621-86-8
Benzoic acid (2R,3S,5R,6S)-2-((2S,3R,5S,6R)-6-acetoxymethyl-3,5-bis-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-5-benzyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / 5percent HCl in MeOH / 0.33 h

2: 91.7 percent / sym-collidine / 0.67 h / -40 °C

3: 93.3 percent / pyridine / Ambient temperature

4: 94.4 percent / 5percent HCl in MeOH / toluene / 2 h / Ambient temperature

5: 93 percent / imidazole / CH₂Cl₂

6: 87.1 percent / tin(IV) chloride, silver perchlorate / heptane; diethyl ether / 24 h / 0 °C

With pyridine; 1H-imidazole; 2,4,6-trimethyl-pyridine; hydrogenchloride; silver perchlorate; tin(IV) chloride; In diethyl ether; n-heptane; dichloromethane; toluene;
DOI:10.1016/0008-6215(96)00005-5