((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester
• CAS No.: 99613-16-8
• Molecular Formula: C₂₈H₂₉NO₆
• Molecular Weight: 475.541
• Mol file: 99613-16-8.mol

Synonyms:((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Chemical Property of ((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

There total 8 articles about ((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl 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: 59.0%

((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester → ((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (99613-16-8)

Guidance literature:

With dipyridinium dichromate; In dichloromethane;

DOI:10.1016/S0040-4039(00)94943-8

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-ribo-hexopyranoside (40773-64-6) → ((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (99613-16-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / pyridine

2: 73 percent / NaN₃ / dimethylformamide

3: H₂; HCl / Pd black / methanol

4: 92 percent / (C₂H₅)3N / methanol

5: 61 percent / NaOH / dimethylformamide

6: 66 percent / c.HCl / acetic acid

7: 59 percent / PDC / CH₂Cl₂

With pyridine; hydrogenchloride; sodium hydroxide; dipyridinium dichromate; sodium azide; hydrogen; triethylamine; palladium; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)94943-8

Reference yield:

Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (14929-15-8) → ((3S,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (99613-16-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / NaN₃ / dimethylformamide

2: H₂; HCl / Pd black / methanol

3: 92 percent / (C₂H₅)3N / methanol

4: 61 percent / NaOH / dimethylformamide

5: 66 percent / c.HCl / acetic acid

6: 59 percent / PDC / CH₂Cl₂

With hydrogenchloride; sodium hydroxide; dipyridinium dichromate; sodium azide; hydrogen; triethylamine; palladium; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)94943-8

upstream raw materials:

methyl 4,6-O-benzylidene-3-deoxy-ribo-hexopyranoside

N-(Benzyloxycarbonyloxy)succinimide

methyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-arabino-hexopyranoside

Toluene-4-sulfonic acid (4aR,6S,7R,8aS)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Downstream raw materials:

(2S,4R,5S)-4,6-Bis-benzyloxy-2-benzyloxycarbonylamino-5-chloro-hexanoic acid methyl ester

(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid

(2S,4R,5R)-4,6-Bis-benzyloxy-2-benzyloxycarbonylamino-5-hydroxy-hexanoic acid methyl ester